Sodium ethoxide → HCID 54548269, compound

HRID 477358Notes

Reaction equation

HRID 477358 reaction equation
CN(C)C(=CC=C(C1C=CC=CC=1)C(OCC)=O)C(OCC)=S.F[B-](F)(F)F.[CH3:29][N:30]([CH3:42])[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:33]=[N+](C)C.CC[O-].[Na+].[CH3:47][C:48]1[CH:49]=[C:50]([CH:59]=[CH:60][CH:61]=1)[CH2:51][S:52][CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55]>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:53]([S:52][CH2:51][C:50]1[CH:59]=[CH:60][CH:61]=[C:48]([CH3:47])[CH:49]=1)[C:54]([O:56][CH2:57][CH3:58])=[O:55])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 53919754HCID 53919754, compoundHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 54548269HCID 54548269, compoundYield 83.4%

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 (3-methylbenzylthio)acetate (7.9 g) in ethanol (100 cc). Diethyl 2-dimethylamino-5-(3-methylbenzylthio)-2,4-hexadienedioate (11 g) is obtained in the form of a brown oil, and is used in the crude state in the subsequent syntheses.

Sources & evidence

ORD record
ord-2597930f8c2e483688869853a7c7ec8c
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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