tert-Butyl carbazate → 1,1-dimethylethyl [(4-chlorophenyl)(1-methyl-1H-benzotriazol-6-yl)-methylene]hydrazine carboxylate

HRID 1288623Notes

Reaction equation

HRID 1288623 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[N:16][N:15]([CH3:18])[C:14]=3[CH:19]=2)=O)=[CH:4][CH:3]=1.[NH:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH2:21]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:21][NH:20][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[N:16][N:15]([CH3:18])[C:14]=3[CH:19]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 189243106-(4-Chlorobenzoyl)-1-methyl-1H-benzotriazole

Product 1

HCID 867524961,1-dimethylethyl [(4-chlorophenyl)(1-methyl-1H-benzotriazol-6-yl)-methylene]hydrazine carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 27.17 g of (4-chlorophenyl)(1-methyl-1H-benzotriazole-6-yl)methanone, 14.24 g of 1,1-dimethylethyl hydrazinecarboxylate and 80 ml of ethanol was stirred for 21 hours at reflux temperature. The reaction mixture was cooled to room temperature and stirring was continued for 2 hours. The precipitate was filtered off, washed with ethanol and dried in vacuo at 50° C., yielding 22.8 g (59.2%) of 1,1-dimethylethyl [(4-chlorophenyl)(1 -methyl-1H-benzotriazol-6-yl)-methylene]hydrazine carboxylate (interm. 1-b).

Workup

  1. temperatureat reflux temperature
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. filtrationThe precipitate was filtered off
  5. washwashed with ethanol
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-a1244270bfea4e1b8f02a7b572c7861c
Source dataset
uspto-grants-1998_05
Patent number
US05746840

Reaction notes

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