Ethyl p-methylbenzenesulfonate → 2,4-Dimethyl-3-ethyl-5-ethoxycarbonyl-thiazolium p-toluene-sulfonate

HRID 1089405Notes

Reaction equation

HRID 1089405 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N)(=S)C.[CH3:15][C:16]1[S:17][CH:18](C(OCC)=O)[CH:19](C)[N:20]=1.[C:27]1([CH3:39])[CH:32]=[CH:31][C:30]([S:33]([O:36]CC)(=[O:35])=[O:34])=[CH:29][CH:28]=1>>[C:27]1([CH3:39])[CH:28]=[CH:29][C:30]([S:33]([O-:36])(=[O:34])=[O:35])=[CH:31][CH:32]=1.[CH3:15][C:16]1[S:17][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH3:10])[N+:20]=1[CH2:19][CH3:18]

Participants

5

Reactant 4

HCID 6638Ethyl p-methylbenzenesulfonateHCID 11858Ethyl 2-chloroacetoacetateHCID 2723949ThioacetamideHCID 221590512,4-Dimethyl-5-ethoxycarbonyl-thiazoline

Product 1

HCID 221590452,4-Dimethyl-3-ethyl-5-ethoxycarbonyl-thiazolium p-toluene-sulfonate

Procedure

Ethyl 2-chloro-acetoacetate is condensed with thioacetamide to 2,4-dimethyl-5-ethoxycarbonyl-thiazoline which is reacted, analogously to Preparation Example 1 A, with ethyl p-toluenesulfonate to give the p-toluenesulfonate of the quaternary ammonium base.

Sources & evidence

ORD record
ord-40fc183093f744f5a69812150e3e369b
Source dataset
uspto-grants-1990_10
Patent number
US04966828

Reaction notes

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