Sodium hydride → HCID 19087704, compound

HRID 1464276Notes

Reaction equation

HRID 1464276 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][Cl:27]>CN(C)C=O>[Cl:27][CH2:26][CH2:25][CH2:24][CH2:23][N:6]([C:7]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 19087683Methyl 2-[(ethoxycarbonyl)amino]-4-nitrobenzoate

Product 1

HCID 19087704HCID 19087704, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-ethoxycarbonylamino-4-nitrobenzoate (4.00 g) in dry dimethylformamide (40 ml) was added sodium hydride (715 mg, 60% oil suspension) in several portions on an ice-bath. After stirring for 1 hour, 1-bromo-4-chlorobutane (2.81 g) was added thereto, and the resulted mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The extract was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (180 g). Elution with a mixed solvent of hexane and ethyl acetate (3:1 V/V) gave methyl 2-[N-(4-chlorobutyl)-N-ethoxycarbonylamino]-4-nitrobenzoate (2.30 g) as an oil.

Workup

  1. stirringthe resulted mixture was stirred for 18 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed in turn with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (180 g)
  7. washElution with a mixed solvent of hexane and ethyl acetate (3:1 V/V)

Sources & evidence

ORD record
ord-e2f8092cdcdc4947a14d784187d458ea
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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