Acetic acid, (phenylthio)-, ethyl ester → Ethyl 5-dimethylamino-5-phenyl-2-phenylthio-2,4-pentadienoate

HRID 477323

Reaction equation

HRID 477323 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=O)[C:4](OCC)=S.F[B-](F)(F)F.CN(C)[C:31]([C:37]1C=CC=[CH:39][CH:38]=1)=[CH:32]C=[N+](C)C.CC[O-].[Na+].C1([S:54]CC(OCC)=O)C=CC=CC=1>C(O)C>[CH3:23][N:2]([CH3:1])[C:3]([C:4]1[CH:39]=[CH:38][CH:37]=[CH:31][CH:32]=1)=[CH:9][CH:10]=[C:11]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:12]([O:14][CH2:15][CH3:16])=[S:54]

Participants

6

Reactant 4

HCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 2723922Sodium ethoxideHCID 75556698N-(3-dimethylamino-3-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 86743587Ethyl 5-dimethylamino-5-phenyl-2-phenylthio-2,4-pentadienoate

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-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborate (15.4 g), a 2M solution of sodium ethylate (26.5 cc) and ethyl (phenylthio)acetate (10.4 g) in ethanol (150 cc). After purification by chromatography on a silica column with dichloromethane as eluent, ethyl 5-dimethylamino-5-phenyl-2-phenylthio-2,4-pentadienoate (9.7 g), m.p. 99° C., is obtained.

Workup

  1. customAfter purification by chromatography on a silica column with dichloromethane as eluent

Sources & evidence

ORD record
ord-97f816d2b43d47fe86176dd1cb1f7ea9
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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