Phosgene → HCID 11965697, compound

HRID 1894040Notes

Reaction equation

HRID 1894040 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:15])[CH2:11][CH2:12][O:13][CH3:14])[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].[C:22](Cl)(Cl)=[O:23]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:15])[CH2:11][CH2:12][O:13][CH3:14])[C:7]([C:16]([F:17])([F:19])[F:18])=[CH:6][C:5]=1[N:20]=[C:22]=[O:23]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 11965696HCID 11965696, compound

Product 1

HCID 11965697HCID 11965697, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a dried flask purged with argon, a solution of 2-amino-5-(3-methoxy-propionyl)-4-trifluoromethyl-benzoic acid methyl ester (154 mg, 0.504 mmol) in dry toluene (4.7 mL) was cooled to 0° C. and treated dropwise with a solution of phosgene in toluene (20%, 4.9 mL). A slow stream of phosgene was introduced and the reaction mixture was heated to reflux for 2 h. Argon was blown through the yellow solution and the solvent distilled off leaving the title compound (168 mg, 100%) as an oily residue, sufficiently pure for the next step. 1H-NMR (CDCl3, 360 MHz): 8.20 (s, 1H), 7.45 (s, 1H), 4.00 (s, 3H), 3.75 (t, J=8 Hz, 2H), 3.35 (s, 3H), 3.10 (t, J=8 Hz, 2H).

Workup

  1. customIn a dried flask purged with argon
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2 h
  4. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-08683da7b2434ed89e33be1404bea74b
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

Loading…