2,4-Dichloroaniline → HCID 20030121, compound

HRID 622663Notes

Reaction equation

HRID 622663 reaction equation
[N:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)=[N+:2]=[N-:3].S(Cl)(Cl)=O.[Cl:18][C:19]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:20]=1[NH2:21]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[N:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([NH:21][C:20]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:19]=1[Cl:18])=[O:8])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 111232,4-DichloroanilineHCID 24386Thionyl ChlorideHCID 11171598HCID 11171598, compound

Product 1

HCID 20030121HCID 20030121, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

2-Azido-4-chlorobenzoic acid (130 g) was stirred with thionyl chloride (52 ml) in dry toluene at room temperature for 24 hours. The solution was evaporated to give crude 2-azido-4-chlorobenzoyl chloride. This product (14.2 g) was added to a solution of 2,4-dichloroaniline (10.65 g) in dry pyridine (70 ml) and the mixture stirred for 25 mins. It was then poured into ice-water and the precipitate filtered off, washed with water, sucked dry, heated in boiling ethanol and the residue filtered off, washed with ethanol and air-dried to give 2-azido-4-chloro-N-(2,4-dichlorophenyl)benzamide, m.p. 169.5° C. (dec.)

Workup

  1. customThe solution was evaporated
  2. customto give crude 2-azido-4-chlorobenzoyl chloride
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customsucked dry
  6. temperatureheated
  7. filtrationthe residue filtered off
  8. washwashed with ethanol
  9. customair-dried

Sources & evidence

ORD record
ord-3fb5bdee6c5948ed84814aafcdb61de0
Source dataset
uspto-grants-1988_09
Patent number
US04772613

Reaction notes

Loading…