Acetic acid, (ethylthio)-, ethyl ester → HCID 86743596, compound

HRID 477361Notes

Reaction equation

HRID 477361 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1C=CC=C[CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[S:5].F[B-](F)(F)F.CN(C)C(C(OCC)=O)=CC=[N+](C)C.CC[O-].[Na+].C(SCC(OCC)=O)C>C(O)C>[CH3:23][N:2]([CH3:1])[C:3](=[CH:9][CH:10]=[C:11]([CH2:17][CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[S:5]

Participants

6

Reactant 4

HCID 350365Acetic acid, (ethylthio)-, ethyl esterHCID 2723922Sodium ethoxideHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 86743596HCID 86743596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (10 g), a 2M ethanolic solution of sodium ethylate (21 cc) and ethyl (ethylthio)acetate (5.2 g) in ethanol (100 cc). Diethyl 2-dimethylamino-5-ethylthio-2,4-hexadienedioate (8.5 g) is thereby obtained in the form of a red oil, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-501af97a99164b36a02f6bdeee3ca82e
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

Loading…