Phosphorus oxychloride → 5-Acetylamino-2-chloro-4-(4-chlorosulfonyl-2-methylsulfonylphenylazo)phenol

HRID 1252025Notes

Reaction equation

HRID 1252025 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([S:25]([O-:28])(=O)=[O:26])[CH:8]=[CH:9][C:10]=1[N:11]=[N:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[CH:15][C:14]=1[NH:21][C:22](=[O:24])[CH3:23])(=[O:4])=[O:3].[Ca+2].CS(C1C=C(S([O-])(=O)=O)C=CC=1N=NC1C=C([Cl:48])C(O)=CC=1NC(=O)C)(=O)=O.CC(N(C)C)=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:22]([NH:21][C:14]1[C:13]([N:12]=[N:11][C:10]2[CH:9]=[CH:8][C:7]([S:25]([Cl:48])(=[O:28])=[O:26])=[CH:6][C:5]=2[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:18][C:17]([Cl:19])=[C:16]([OH:20])[CH:15]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 136342787Calcium 3-methylsulfonyl-4-(2-acetylamino-5-chloro-4-hydroxyphenylazo)phenylsulfonate

Product 1

HCID 1355831435-Acetylamino-2-chloro-4-(4-chlorosulfonyl-2-methylsulfonylphenylazo)phenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 18 g of calcium 3-methylsulfonyl-4-(2-acetylamino-5-chloro-4-hydroxyphenylazo)phenylsulfonate, 25 ml of dimethylacetamide, and 54 ml of acetonitrile was added dropwise to 18 ml of phosphorus oxychloride at room temperature with stirring. After completion of the addition, the reaction was allowed to proceed at 60° C. for 3 hours, and the reaction mixture was cooled to room temperature and then poured in 1 l of ice water. The mixture was stirred at a temperature of 10° C. or less for 1 hour and the resulting crystalline precipitate was collected by filtration, washed with water and air-dried.

Workup

  1. additionAfter completion of the addition
  2. stirringThe mixture was stirred at a temperature of 10° C. or less for 1 hour
  3. filtrationthe resulting crystalline precipitate was collected by filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-99c79e2056094d54863bae3180c3fe18
Source dataset
uspto-grants-1988_05
Patent number
US04741997

Reaction notes

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