2-(p-Methoxybenzyloxy)acetic acid hydrazide → 2-chloro-4-(o-chlorophenyl)-9-[(p-methoxybenzyloxy)methyl]-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

HRID 262987Notes

Reaction equation

HRID 262987 reaction equation
[Cl:1][C:2]1[S:19][C:5]2[NH:6][C:7](=S)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[CH3:20][O:21][C:22]1[CH:34]=[CH:33][C:25]([CH2:26][O:27][CH2:28][C:29]([NH:31][NH2:32])=O)=[CH:24][CH:23]=1>C(O)CCC>[Cl:1][C:2]1[S:19][C:5]2[N:6]3[C:29]([CH2:28][O:27][CH2:26][C:25]4[CH:33]=[CH:34][C:22]([O:21][CH3:20])=[CH:23][CH:24]=4)=[N:31][N:32]=[C:7]3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 204730792-(p-Methoxybenzyloxy)acetic acid hydrazideHCID 1357830787-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno-(2,3-e)-(1,4)-diazepine-2-thione

Product 1

HCID 213177152-chloro-4-(o-chlorophenyl)-9-[(p-methoxybenzyloxy)methyl]-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1.5 g of 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-thione are refluxed for 4 hours with 4 g of 2-(p-methoxybenzyloxy)acetic acid hydrazide in 100 ml of absolute butanol, a nitrogen stream being conducted through the solution. The mixture is evaporated, taken up in methylene chloride, washed with water and saturated sodium chloride solution, dried and evaporated. By recrystallization of the residue from ethyl acetate containing active carbon, there is obtained 2-chloro-4-(o-chlorophenyl)-9-[(p-methoxybenzyloxy)methyl]-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine.

Workup

  1. customThe mixture is evaporated
  2. washwashed with water and saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. customBy recrystallization of the residue from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-f2a1760115e54ae9ae72c949ec630377
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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