Thionyl Chloride → alpha-(2-Acetoxy-5-chlorosulfonylphenylazo)acetoacetanilide

HRID 26122Notes

Reaction equation

HRID 26122 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](O)(=[O:13])=[O:12])=[CH:7][C:6]=1[N:15]=[N:16][CH:17]([C:27]([CH3:29])=[O:28])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])(=[O:3])[CH3:2].S(Cl)([Cl:32])=O>CN(C)C=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([Cl:32])(=[O:13])=[O:12])=[CH:7][C:6]=1[N:15]=[N:16][CH:17]([C:27]([CH3:29])=[O:28])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23336111alpha-(2-Acetoxy-5-sulfophenylazo)acetoacetanilide

Product 1

HCID 23336104alpha-(2-Acetoxy-5-chlorosulfonylphenylazo)acetoacetanilide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

α-(2-Acetoxy-5-sulfophenylazo)acetoacetanilide (20 g) was added to thionyl chloride (100 ml). After the addition of dimethylformamide (4 ml), solution was complete, then followed by precipitation of the product. It was filtered off and dried in the vacuum oven at 40° C. Yield: 16.7 g, m.p. 225° to 226° C.

Workup

  1. customfollowed by precipitation of the product
  2. filtrationIt was filtered off
  3. customdried in the vacuum oven at 40° C

Sources & evidence

ORD record
ord-cf01d4de27e3487eac128ffce1345f33
Source dataset
uspto-grants-1979_04
Patent number
US04148643

Reaction notes

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