4-Chlorophenyl Isocyanate → HCID 57650113, compound

HRID 2063466Notes

Reaction equation

HRID 2063466 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]([C@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)=[N:11][N:10]=[C:9]2[CH3:18])=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:9]([CH3:18])=[N:10][N:11]=[C:12]2[C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=2)=[O:30])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 81531DiisopropylethylamineHCID 688114841140496-10-1

Product 1

HCID 57650113HCID 57650113, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole hydrochloride (58 mg, 0.2 mmol) was dissolved in dichloromethane (2 ml). 4-chlorophenyl isocyanate (0.031 ml, 0.2 mmol) and N,N-diisopropylethylamine-(0.050 ml) were added while stirring. The reaction mixture was stirred for 12 h then evaporated to dryness. Purification by silica gel column chromatography (methanol/dichloromethane gradient, 0-15% methanol) afforded the desired product as a white amorphous solid (75.1 mg, 87%).

Workup

  1. stirringThe reaction mixture was stirred for 12 h
  2. customthen evaporated to dryness
  3. customPurification by silica gel column chromatography (methanol/dichloromethane gradient, 0-15% methanol)

Sources & evidence

ORD record
ord-b7b3306522b54094b3874f234a31e9c7
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…