4-Bromophenyl isocyanate → N-(4-bromophenyl)-2-{[1-(cyclopropylcarbonyl)-3-azetidinyl]acetyl}hydrazinecarboxamide

HRID 525187Notes

Reaction equation

HRID 525187 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:9][CH:8]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>ClCCl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:14][NH:13][C:11](=[O:12])[CH2:10][CH:8]2[CH2:7][N:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:9]2)=[O:24])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 673539452-[1-(Cyclopropylcarbonyl)-3-azetidinyl]acetohydrazide

Product 1

HCID 67354249N-(4-bromophenyl)-2-{[1-(cyclopropylcarbonyl)-3-azetidinyl]acetyl}hydrazinecarboxamideYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, a solution of 2-[1-(cyclopropylcarbonyl)-3-azetidinyl]acetohydrazide (0.316 g, 1.602 mmol) in dichloromethane (10 mL) was treated with 4-bromophenylisocyanate (0.317 g, 1.602 mmol) and the reaction mixture was stirred at room temperature for 1 h (white precipitate formed). The white solid was filtered, rinsing with cold dichloromethane (4×), and dried under air suction to give the title compound (0.455 g, 87% pure, 62% yield). MS(ES)+ m/e 394.9, 396.6 [M+H]+.

Workup

  1. custom(white precipitate formed)
  2. filtrationThe white solid was filtered
  3. washrinsing with cold dichloromethane (4×)
  4. customdried under air suction

Sources & evidence

ORD record
ord-e8fe0e871cdf4ca69f91913355342ade
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

Loading…