Dimethylformamide → HCID 13393800, compound

HRID 2107726Notes

Reaction equation

HRID 2107726 reaction equation
[C:1]1([CH:7]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH2:8][C:9](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:23])=O.CN(C)[CH:28]=[O:29]>>[Cl:23][C:9]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[S:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]=1[CH:28]=[O:29]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 54242261HCID 54242261, compound

Product 1

HCID 13393800HCID 13393800, compound

Procedure

As in example 18,but using 4.3 g 3-phenyl-3-(2-methoxyphenylmercapto)propionic acid, 40 ml dimethylformamide and 15 ml phosphorous oxychloride. After hydrolysis and work-up the residual oil is filtered over a small silicagel column and the residual solid is recrystallized in a mixture of hexane and ethyl acetate. Pure 4-chloro-3-formyl-8-methoxy-thioflav-3-ene is obtained as yellow crystals; m.p. 128°-130° C.

Workup

  1. customAfter hydrolysis
  2. filtrationis filtered over a small silicagel column
  3. customthe residual solid is recrystallized in a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-8f083086236148598c7dd865946502c3
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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