3-Amino-4-chlorobenzoic acid → HCID 22645713, compound

HRID 2414358Notes

Reaction equation

HRID 2414358 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].C(N(C(C)C)CC)(C)C.[Cl:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([N:26]=[C:27]=[O:28])=[O:25]>ClCCl>[Cl:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:27]([NH:26][C:24](=[O:25])[C:23]1[CH:29]=[CH:30][CH:31]=[CH:32][C:22]=1[Cl:21])=[O:28]

Participants

5

Reactant 3

HCID 760923-Amino-4-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 99423112-Chlorobenzoyl isocyanate

Product 1

HCID 22645713HCID 22645713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (5.8 mmol) of 3-amino-4-chlorobenzoic acid were mixed with 0.75 g (5.8 mmol) of diisopropylethylamine and 1.06 g (5.8 mmol) of 2-chlorobenzoyl isocyanate in 5 ml of dichloromethane and reacted at room temperature for 12 hours. The solvent was evaporated, the residue was mixed with 5% strength sodium bicarbonate solution and extracted twice with diethyl ether, and the aqueous phase was adjusted to pH 3 with HCl. The resulting precipitate was filtered off with suction.

Workup

  1. customreacted at room temperature for 12 hours
  2. customThe solvent was evaporated
  3. additionthe residue was mixed with 5% strength sodium bicarbonate solution
  4. extractionextracted twice with diethyl ether
  5. filtrationThe resulting precipitate was filtered off with suction

Sources & evidence

ORD record
ord-20bee2b9c73043cbb0d8b254a1aa59e3
Source dataset
uspto-grants-2004_11
Patent number
US06812250B2

Reaction notes

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