Tert-butyl 2-(4-cyanophenyl)hydrazinecarboxylate → Tert-butyl 2-((2-chloro-6-fluorobenzoyl)carbamoyl)-2-(4-cyanophenyl)hydrazinecarboxylate

HRID 59255Notes

Reaction equation

HRID 59255 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].[Cl:18][C:19]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:20]=1[C:21]([N:23]=[C:24]=[O:25])=[O:22]>C(Cl)Cl>[Cl:18][C:19]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:20]=1[C:21]([NH:23][C:24]([N:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:25])=[O:22]

Participants

4

Reactant 2

HCID 11207040Tert-butyl 2-(4-cyanophenyl)hydrazinecarboxylateHCID 130517312-Chloro-6-fluorobenzoyl isocyanate

Product 1

HCID 90019599Tert-butyl 2-((2-chloro-6-fluorobenzoyl)carbamoyl)-2-(4-cyanophenyl)hydrazinecarboxylateYield 92,414.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-cyanophenyl)hydrazinecarboxylate (2.5 g, 0.01 mmol) in DCM (15 mL) was added 2-chloro-6-fluorobenzoyl isocyanate (Intermediate-8, 2.56 g, 0.012 mmol). The reaction mass was stirred at RT for 2 h. Excess of solvent was removed under vacuum to afford 4.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 1.42 (s, 9H), 7.25-7.38 (m, 2H), 7.47-7.60 (m, 3H), 7.82-7.85 (m, 2H), 9.96 (br s, 1H), 11.43 (br s, 1H); MS (m/z): 431.02 (M+H)+.

Workup

  1. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-757b477a9a2c4ff4a9b727c4bcd756cf
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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