m-Tolyl isocyanate → HCID 67727824, compound

HRID 963051Notes

Reaction equation

HRID 963051 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.[CH3:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>C(Cl)(Cl)Cl>[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:33]([NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([CH3:25])[CH:27]=3)=[O:34])=[N:4][N:5]=[C:6]2[CH2:12][N:11]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 67727814HCID 67727814, compound

Product 1

HCID 67727824HCID 67727824, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9-Aminomethyl-4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (1.07 g) was dissolved in chloroform (50 ml). 3-Methylphenyl isocyanate (0.44 g) was added at room temperature, and the mixture was stirred for 3 hours. The reaction mixture was concentrated, and crystallized from ethyl acetate. The crude crystals were recrystallized from methanol to give 1.47 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)-N'-(3-methylphenyl)urea.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customcrystallized from ethyl acetate
  3. customThe crude crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-1db037e8cc59484db3926ce88f1966ad
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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