Nitromethane → HCID 9798318, compound

HRID 411757Notes

Reaction equation

HRID 411757 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N+:22]([CH3:25])([O-:24])=[O:23].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12](=[O:13])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH:8]=[CH:7][C:3]=1[C:4]([CH2:25][N+:22]([O-:24])=[O:23])=[O:6]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 18541413HCID 18541413, compound

Product 1

HCID 9798318HCID 9798318, compoundYield 1.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was obtained by carrying out the procedure as in Example 42 starting with 19 g (62.5 mmol) of 2-chloro-4-[(2-methylbenzyl)carbonylamino]benzoic acid obtained in step a), 3.18 g of nitromethane, 11 g (67.6 mmol) of diethyl cyanophosphonate, 16.8 g (167 mmol) of triethylamine in 205 ml of DMF dried over a molecular sieve. After chromatography on a silica column (eluent: dichloromethane-methanol 95:5) and recrystallization from a hexane-ethyl acetate mixture, 0.2 g (Yield=1%) of a pale yellow powder is obtained.

Workup

  1. customThis compound was obtained
  2. customdried over a molecular sieve
  3. customAfter chromatography on a silica column (eluent: dichloromethane-methanol 95:5) and recrystallization from a hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-532bed7475314b9b99172fa1151c023e
Source dataset
uspto-grants-2003_05
Patent number
US06559185B2

Reaction notes

Loading…