Dimethylformamide → HCID 59534352, compound

HRID 1422402Notes

Reaction equation

HRID 1422402 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C>C(O)C.[Ni]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:8]([NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:9]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 47448389HCID 47448389, compound

Product 1

HCID 59534352HCID 59534352, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

1-Cyclohexyl-3-(3-nitro-benzyl)-urea (4 g) was suspended in ethanol (70 ml) and Raney nickel (2 g) was added. Under stirring aqueous hydrazine solution (2.5 ml, 80%) was added. DMF was added (50 ml) and the reaction mixture was stirred for additional 2 h and filtered. The solution was evaporated i.v. affording the title compound (3 g, Rf=0.43 DCM/ethanol 19:1).

Workup

  1. additionUnder stirring aqueous hydrazine solution (2.5 ml, 80%) was added
  2. filtrationfiltered
  3. customThe solution was evaporated i.v

Sources & evidence

ORD record
ord-b00a81a637e24c7484f079f5e968f4db
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

Loading…