3-Chloro-2-butanone → 2,5,6-Trimethyl-2,3-dihydro-1,4-dithiine

HRID 1680912Notes

Reaction equation

HRID 1680912 reaction equation
[CH2:1]([SH:5])[CH:2]([SH:4])[CH3:3].Cl[CH:7]([CH3:11])[C:8](=O)[CH3:9]>>[CH3:3][CH:2]1[CH2:1][S:5][C:8]([CH3:9])=[C:7]([CH3:11])[S:4]1

Participants

3

Reactant 2

HCID 200263-Chloro-2-butanoneHCID 612172,3-Dimercaptopropane

Product 1

HCID 129200482,5,6-Trimethyl-2,3-dihydro-1,4-dithiineYield 36.5%

Procedure

The procedure of Example 1(a) is repeated, using 1,2-propanedithiol and 3-chloro-2-butanone to give 2,3-dihydro-2,5,6-trimethyl-1,4-dithiin as a clear green liquid, bp 49.5°-51°/0.7 mm, yield 36.5%, NMR 1.36 (3d), 1.88 (6s), 2.4-3.6 (3m) (CDCl3). IR, 2905 (sh); 1605, 1410 (broad); 1250, 1155 (sh); 1065 (br); 730, 705.

Sources & evidence

ORD record
ord-706f690da3274d1689bb0fc0fd6d2147
Source dataset
uspto-grants-1981_06
Patent number
US04276422

Reaction notes

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