Ethyl (methylthio)acetate → HCID 86743595, compound

HRID 477360Notes

Reaction equation

HRID 477360 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1C=CC=CC=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+].CSCC(OCC)=O>C(O)C>[CH3:23][N:2]([CH3:1])[C:3](=[CH:9][CH:10]=[C:11]([CH3:17])[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 78199Ethyl (methylthio)acetateHCID 2723922Sodium ethoxideHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 86743595HCID 86743595, 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 (28.6 g), a 2M ethanolic solution of sodium ethylate (50 cc) and ethyl (methylthio)acetate (13.4 g) in ethanol (180 cc). Diethyl 2-dimethylamino-5-methylthio-2,4-hexadienedioate (21.9 g) is thereby obtained in the form of a brown oil, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-f59a2217abf242fe8512ca2f37af668b
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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