Water → ethyl N-[(Z)-[1-[3-nitro-4,5-bis(phenylmethoxy)phenyl]-2-[2-(trifluoromethyl)-3-pyridinyl]ethylidene]amino]carbamate

HRID 62018

Reaction equation

HRID 62018 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:26](=O)[CH2:27][C:28]2[C:29]([C:34]([F:37])([F:36])[F:35])=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[NH:40][NH2:41].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[C:26](=[N:41]\[NH:40][C:39]([O:43][CH2:44][CH3:45])=[O:42])/[CH2:27][C:28]2[C:29]([C:34]([F:36])([F:35])[F:37])=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 687038971-(3,4-Bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)ethanone

Product 1

HCID 87588773ethyl N-[(Z)-[1-[3-nitro-4,5-bis(phenylmethoxy)phenyl]-2-[2-(trifluoromethyl)-3-pyridinyl]ethylidene]amino]carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)ethanone (0.485 g, 0.93 mmol), ethyl carbazate (0.11 g, 1.06 mmol) and p-toluene sulfonic acid (4 mg) in toluene (10 mL) was refluxed until distillation of water ceased. The reaction mixture was cooled to room temperature, the solvents were evaporated to dryness, and the crude solid was triturated with diethyl ether (15 mL), filtered and dried yielding (Z)-ethyl 2-(1-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)ethylidene)-hydrazinecarboxylate, 0.475 g (84%).

Workup

  1. customthe solvents were evaporated to dryness
  2. customthe crude solid was triturated with diethyl ether (15 mL)
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-bf696df99e3c42e4bef874a61be84a2e
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Linked notes

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