4-Chloroaniline → HCID 86640285, compound

HRID 1678647Notes

Reaction equation

HRID 1678647 reaction equation
[N:1]([C:4]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([OH:8])=O)=[N+:2]=[N-:3].[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>S(Cl)(Cl)=O.ClCCl>[N:1]([C:4]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([Cl:15])=[CH:17][CH:18]=1)=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 85884212HCID 85884212, compound

Product 1

HCID 86640285HCID 86640285, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-azido-4,5-difluoro-benzoic acid (26.2 g, 132 mmol; Grieder A.; Thomas, A. W., Synthesis (2003), (11), 1707-1711) in thionyl chloride (216 ml) was stirred under reflux conditions for 1.5 h. The solvent was removed under reduced pressure to give the corresponding crude acid chloride which was suspended in dichloromethane (200 ml). 4-Chloroaniline (16.8 g, 132 mmol) was added and the mixture was stirred at ambient temperature for 14 h. Under ice cooling saturated NaHCO3 solution was added until pH 8 was reached. The mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown solid which was crystallized from dichloromethane/n-heptane to give the title compound (18.5 g, 60 mmol; 46%) as yellow crystals.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give the corresponding crude acid chloride which
  3. stirringthe mixture was stirred at ambient temperature for 14 h
  4. additionUnder ice cooling saturated NaHCO3 solution was added until pH 8
  5. extractionThe mixture was extracted two times with dichloromethane
  6. washthe combined extracts were washed with ice water/brine 1/1
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customto give a brown solid which
  10. customwas crystallized from dichloromethane/n-heptane

Sources & evidence

ORD record
ord-38dd46d1ded544c984fa1263f92a3090
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

Loading…