Triethylamine → HCID 67727741, compound

HRID 963048Notes

Reaction equation

HRID 963048 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]2[C:8]3[S:22][C:21]([CH2:23][CH3:24])=[CH:20][C:9]=3[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N:11][CH2:12][C:6]2=[N:5][N:4]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:36](Cl)=[O:37]>ClC(Cl)C>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[C:9]2[CH:20]=[C:21]([CH2:23][CH3:24])[S:22][C:8]=2[N:7]2[C:3]([CH2:2][NH:1][C:36](=[O:37])[C:35]3[CH:39]=[CH:40][C:41]([Cl:42])=[C:33]([Cl:32])[CH:34]=3)=[N:4][N:5]=[C:6]2[CH2:12][N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 67727814HCID 67727814, compound

Product 1

HCID 67727741HCID 67727741, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

9-Aminomethyl-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (0.28 g) and triethylamine (0.115 ml) were dissolved in dichloroethane (15 ml). 3,4-Dichlorobenzoyl chloride (0.17 g) was added at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and methanol as a developing solvent. The obtained solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 0.27 g of N-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-ylmethyl)-3,4-dichlorobenzamide.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography
  3. customThe obtained solid was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d80a206409db4a0ab1e7b3a219128e98
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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