Hydrochloric Acid → 2-Chlorobenzanilide

HRID 1379907Notes

Reaction equation

HRID 1379907 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C1(C)C=CC=CC=1>[C:16]1([NH:15][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 83742-Chlorobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 232652-ChlorobenzanilideYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a 500 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 31.3 g (0.2 mol) of 2-chlorobenzoic acid and 180 g of toluene are placed. To the above mixture in the flask, 25.0 g (0.21 mol) of thionyl chloride is added dropwise over 30 minutes while stirring at a temperature of from 60° to 65° C. to be allowed to react with each other for about 30 minutes. To the above reaction mixture, a solution containing 27.9 g (0.3 mol) of aniline dissolved in 100 g of toluene is dropwise added to be allowed to react with each other at a temperature of from 70° to 75° C. for 30 minutes. After completion of the reaction, the reaction mixture is cooled to room temperature, and 70 g of a 5% by weight hydrochloric acid solution is added to the above mixture. The mixture is vigorously shaken and kept standing for separation of the toluene layer from the aqueous layer. After separation of the toluene layer, it is condensed to precipitate white crystals, followed by recrystallization (in a water/methanol mixture of 3/7), to give 43.1 g of N-phenyl-2-chlorobenzamide (melting point: 116° to 117° C.). The yield of the product against 2-chlorobenzoic acid is 93%.

Workup

  1. customTo a 500 ml four-necked flask equipped with a stirrer
  2. customto react with each other for about 30 minutes
  3. additionis dropwise added
  4. customto react with each other at a temperature of from 70° to 75° C. for 30 minutes
  5. customAfter completion of the reaction
  6. stirringThe mixture is vigorously shaken
  7. customkept standing for separation of the toluene layer from the aqueous layer
  8. customAfter separation of the toluene layer, it
  9. customcondensed
  10. customto precipitate white crystals
  11. customfollowed by recrystallization (
  12. additionin a water/methanol mixture of 3/7),

Sources & evidence

ORD record
ord-1388067e51af4407871cb2537ce3ffc1
Source dataset
uspto-grants-1997_09
Patent number
US05672751

Reaction notes

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