Hansen, Bertil’s team published research in Acta Chemica Scandinavica in 13 | CAS: 4584-49-0

Hansen, Bertil published the artcilePreparation of thiocholine esters. II. Esters of α- and β-methylthiocholine, Category: chlorides-buliding-blocks, the publication is Acta Chemica Scandinavica (1959), 159-62, database is CAplus.

cf. CA 52, 14538g. α-Methyl- and β-methylthiocholine halide esters of benzoic and the lower fatty acids were prepared in good yield from Me₂NCHMeCH₂SH (I), b₈₈ 71°, n²⁵_D 1.4538, d₂₅ 0.8693, and HSCHMeCH₂NMe₂ (II), b₇₀ 78.5°, n²⁵_D 1.4684, d₂₀ 0.9046, resp., by esterification with Ac₂O and quaternization with MeI. The α-Me esters were also prepared from 1,2-propylene sulfide by adding the acid bromide and then quaternizing with Et₃N. The II was synthesized (Renshaw, et al., CA 32, 7412¹) from Me₂NCH₂CHMeCl.HCl (III), m. 185°, and (H₂N)₂CS. An attempt to prepare I similarly from MeCHNMe₂CH₂Cl.HCl and (H₂N)₂CS gave only II; addition of Me₂NH to propylene sulfide, b₁ 74-6° (prepared in 58% yield from propylene oxide and (H₂N)₂CS, in Et₂O gave I as the only product. Esters of MeCHBrCH₂SH prepared were: 73% acetate, b₆ 72-3°; 66% propionate, b₉ 93-6°; 53% butyrate, b₈ 99.5-100.5°; and 53% valerate, b₁₀ 125-6.5°. Esters of α-methylthiocholine bromide: 63% acetate, m. 187°; 63% propionate, m. 154°; 54% butyrate, m. 170°; and 67% valerate, m. 179°. Also prepared were the acetate, b₁₁ 64.5-6°, propionate, b₁₂ 67-81°, butyrate, b₉ 80-8°, isobutyrate, b₁₀ 85-94°, valerate, b_0.07 53-60°, and benzoate, b_0.01 88-96°, of I, and the acetate, b₁₁ 76-82°, propionate, b₁₀ 78-88°, butyrate, b_1.8 74-85°, isobutyrate, b₁₂ 86-92°, valerate, b_0.3, and benzoate, b_0.03 120-5°, of II. α-Methylthiocholine bromide acetate, m. 188°, and the following β-methylthiocholine bromide esters (acetate, m. 168°, 67% butyrate, m. 164°, and 32% isobutyrate, m. 140°), α-methylthiocholine iodide esters (50% acetate, m. 164°, 61% propionate, m. 155°, 62% butyrate, m. 130°, 82% isobutyrate, m. 158°, 62% valerate, m. 152°, and 54% benzoate, m. 136°), and β-methylthiocholine iodide esters (70% acetate, m. 150°, 65% propionate, m. 132°, 67% butyrate, m. 164°, 32% isobutyrate, m. 140°, 31% valerate, m. 74°, and 76% benzoate, m. 194°) were prepared III refluxed 65 h. with (H₂N)₂CS in absolute EtOH gave 52% S-(1-dimethylamino-2-propyl)isothiuronium chloride hydrochloride, m. 154° (PrOH).

Acta Chemica Scandinavica published new progress about 4584-49-0. 4584-49-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Salt,Amine,Aliphatic hydrocarbon chain, name is 2-Chloro-N,N-dimethylpropan-1-amine hydrochloride, and the molecular formula is C5H13Cl2N, Category: chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics