Triethylamine → 3-Chloro-4-isocyanato-benzoic acid methyl ester

HRID 1690520Notes

Reaction equation

HRID 1690520 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([Cl:23])[CH:17]=1.CCN(CC)CC>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:2]=[O:4])=[C:18]([Cl:23])[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Product 1

HCID 866402623-Chloro-4-isocyanato-benzoic acid methyl esterYield 260%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of triphosgene (59 mg, 200 μmol) in CH2Cl2 (1.5 ml) was added 4-amino-3-chloro-benzoic acid methyl ester (100 mg, 540 μmol; [84228-44-4]) and a solution of Et3N (150 μl, 1.1 mmol) in CH2Cl2 (0.5 ml) under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 30 min. The solvent was removed under reduced pressure. The residue was triturated with EtOAc, the solid was filtered off and the filtrate was evaporated to dryness under reduced pressure to give the title compound (111 mg, 520 μmol; 97%) as brown solid which was used in the next step without further purification. MS: m/e=228.9 [M+H+].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with EtOAc
  3. filtrationthe solid was filtered off
  4. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7c4182d323064c5e97fea1ac77f19710
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

Loading…