Toluene → HCID 23335066, compound

HRID 903811Notes

Reaction equation

HRID 903811 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH2:18].C1(C)C=CC=CC=1>[OH-].[Na+]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:13])(=[O:12])[NH:18][C:17]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:16]=2[Cl:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 111232,4-DichloroanilineHCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-

Product 1

HCID 23335066HCID 23335066, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

602 Parts of 2-chloro-5-chlorosulfonylbenzoic acid are added to a solution of 830 parts of 2,4-dichloroaniline in 600 parts of toluene at 60° and the mixture is stirred for 6 hours at the same temperature. Insoluble material is then dissolved in dilute sodium hydroxide solution, the aqueous layer is separated off and acidified with dilute hydrochloric acid and the product is filtered off and washed with water. After redissolving in sodium hydroxide solution, reprecipitation with hydrochloric acid and drying, 592 parts of 2-chloro-5-[2,4-dichlorophenyl-sulfamoyl]-benzoic acid are obtained as a colorless powder of melting point 174° C.

Workup

  1. customthe aqueous layer is separated off
  2. filtrationthe product is filtered off
  3. washwashed with water
  4. dissolutionAfter redissolving in sodium hydroxide solution
  5. customreprecipitation with hydrochloric acid
  6. customdrying

Sources & evidence

ORD record
ord-8db81390f00b4b0aa6f3146dde7e67a5
Source dataset
uspto-grants-1980_10
Patent number
US04229343

Reaction notes

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