4-Chloroaniline → HCID 86640271, compound

HRID 1690589Notes

Reaction equation

HRID 1690589 reaction equation
[N:1]([C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])=[N+:2]=[N-:3].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]([C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:5]=1[C:6]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 516892Sodium BicarbonateHCID 86640269HCID 86640269, compound

Product 1

HCID 86640271HCID 86640271, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Azido-4-fluoro-benzoic acid (3.01 g, 17 mmol; Barral, Karine; Moorhouse, Adam D.; Moses, John E. Organic Letters (2007), 9(9), 1809-1811) was dissolved at ambient temperature in thionyl chloride (27.3 ml) under an argon atmosphere. The reaction mixture was heated to 80° C. for 1.5 h and brought to dryness under reduced pressure to give 2-azido-4-fluoro-benzoyl chloride as orange oil. 2-Azido-4-fluoro-benzoyl chloride was dissolved at ambient temperature in CH2Cl2 (23 ml) under an argon atmosphere. 4-Chloro-phenylamine (2.12 g, 17 mmol; [106-47-8]) was added and the reaction mixture was stirred at ambient temperature for 14 h. Saturated aqueous NaHCO3 solution was added until a pH of 8 was adjusted, the layers were separated and the aqueous layer was extracted two more times with CH2Cl2. 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 heptane/CH2Cl2 to give the title compound (3.08 g, 11 mmol; 64%) as off-white crystals. MS: m/e=291.0 [M+H+].

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted two more times with CH2Cl2
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto give a brown solid which
  7. customwas crystallized from heptane/CH2Cl2

Sources & evidence

ORD record
ord-541823c797db42a4bdeab0fe38a1b548
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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