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

HRID 2052198Notes

Reaction equation

HRID 2052198 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-1e23badd5e464a70944d12ae6e208986
Source dataset
uspto-grants-1980_01
Patent number
US04183755

Reaction notes

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