Triethylamine → HCID 9822333, compound

HRID 991423Notes

Reaction equation

HRID 991423 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH:16]=[CH:17][C:18]=1[Cl:19].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:19][C:18]1[CH:17]=[CH:16][C:15]([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)=[CH:14][C:13]=1[NH:12][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 16793499HCID 16793499, compound

Product 1

HCID 9822333HCID 9822333, compoundYield 173.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Cyanobenzoyl chloride (0.25 g) was added to a stirred mixture of N-(3-amino-4-chlorophenyl)-4-cyanobenzamide (0.39 g), triethylamine (0.51 ml), 4-dimethylaminopyridine (0.01 g) and methylene chloride (25 ml). The mixture was stirred at ambient temperature for 18 hours. The mixture was washed with 2M hydrochloric acid solution and with water. The organic phase was dried (MgSO4)and evaporated. The residue was purified by column chromatography on silica gel using a 49:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.1 1 g);

Workup

  1. washThe mixture was washed with 2M hydrochloric acid solution and with water
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica gel using
  4. additiona 49:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-be7c5976a5bc497e87e235d4c7d1dd7f
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

Loading…