Acetyl chloride → HCID 21717741, compound

HRID 1386923Notes

Reaction equation

HRID 1386923 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH2:18][NH2:19])[N:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH2:18][NH:19][C:30](=[O:32])[CH3:31])[N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21717734HCID 21717734, compound

Product 1

HCID 21717741HCID 21717741, compoundYield 794.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzylamine hydrochloride (1:1) (50 mg, 0.016 mmol) and triethylamine (32 mg, 0.032 mmol) in CH2Cl2 (5 ml) was stirred at r.t. for 30 min. Acetyl chloride (12 mg, 0.016 mmol) was then added and the mixture stirred for 1.5 hrs. The reaction mixture was evaporated and chromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 96:4. This afforded a yellow oil, which was then dried under high vacuum at 50° C. to afford the title compound (41 mg, 72% yield) as a light yellow solid. MS: m/e=323.3 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. customchromatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 96:4
  3. customThis afforded a yellow oil, which
  4. customwas then dried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-d67029d4fad64e87bad5fdce0ab60285
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

Loading…