Sodium ethoxide → HCID 86743601, compound

HRID 1074089Notes

Reaction equation

HRID 1074089 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1[CH:22]=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>C(O)C>[CH3:23][N:2]([CH3:1])[C:3](=[CH:9][CH:10]=[C:11]([CH:17]([CH3:18])[CH3:22])[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 2723922Sodium ethoxideHCID 10773300ethyl (isopropylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 86743601HCID 86743601, 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 (17.5 cc) and ethyl (isopropylthio)acetate (5.7 g) in ethanol (57 cc). Diethyl 2-dimethylamino-5-isopropylthio-2,4-hexadienedioate (9.8 g) is thereby obtained in the form of an orange-coloured oil, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-76b7ca40ba044979b89e48d508bb4506
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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