Benzene, 1-isocyanato-2-methoxy- → N-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)-N'-(2-methoxyphenyl)urea

HRID 863407Notes

Reaction equation

HRID 863407 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:6]2[C:16]([CH3:20])=[C:17]([CH3:19])[S:18][C:5]=2[N:4]2[C:21]([CH3:24])=[N:22][N:23]=[C:3]12.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>C(Cl)(Cl)Cl>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[C:6]3[C:16]([CH3:20])=[C:17]([CH3:19])[S:18][C:5]=3[N:4]3[C:21]([CH3:24])=[N:22][N:23]=[C:3]3[CH:2]([NH:1][C:34]([NH:33][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH3:25])=[O:35])[N:8]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 196961326-Amino-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 9914185N-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)-N'-(2-methoxyphenyl)urea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Amino-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2- f][1,2,4]triazolo[4,3-a][1,4]diazepine (4 g) was dissolved in chloroform (30 ml). 2-Methoxyphenyl isocyanate (1.7 ml) was added, and the mixture was stirred for 30 minutes. The reaction mixture was subjected to silica gel column chromatography, and the resultant crystals were recrystallized from ethanol to give 5.14 g of N-(4-(4-chlorophenyl)-2,3,9- trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin- 6-yl)-N'-(2-methoxyphenyl)urea, melting point 261°-262° C.

Workup

  1. customthe resultant crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-fbbab2a9c80b482a963849bc73b49c45
Source dataset
uspto-grants-1998_02
Patent number
US05721231

Reaction notes

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