3,4-Diaminobenzoic acid → HCID 68805970, compound

HRID 855787Notes

Reaction equation

HRID 855787 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].[Cl:12][C:13]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:14]=1[C:15]([N:17]=[C:18]=[O:19])=[O:16].ClCCl>CN1CCCC1=O>[NH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:18]([NH:17][C:15](=[O:16])[C:14]1[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:13]=1[Cl:12])=[O:19]

Participants

4

Reactant 2

HCID 692633,4-Diaminobenzoic acidHCID 86592174HCID 86592174, compound

Product 1

HCID 68805970HCID 68805970, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

150 mg (1 mmol) of 3,4-diaminobenzoic acid were dissolved in 2 ml of N-methyl-2-pyrrolidinone and, at 0° C., 1 ml (1.2 mmol) of the 2-chloro-4-fluorobenzoyl isocyanate/dichloromethane solution prepared in stage a was added. The resulting precipitate was filtered off with suction. The crude mixture (500 mg) was purified by column chromatography (dichloromethane/methanol=98/2 to 93/7). 80 mg (25%) of the desired product were obtained.

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. customThe crude mixture (500 mg) was purified by column chromatography (dichloromethane/methanol=98/2 to 93/7)

Sources & evidence

ORD record
ord-b11d67b190144e78903634fce37e1800
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Reaction notes

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