Triethylamine → HCID 53818659, compound

HRID 987490Notes

Reaction equation

HRID 987490 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].C(N(CC)CC)C.Cl[C:20](=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:7][C:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:27])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742185-Chloro-2-nitroanilineHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 53818659HCID 53818659, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-nitroaniline (25.4 g, 147 mmol) in N,N-dimethylformamide (300 ml) were added triethylamine (22.6 ml, 162 mmol) and ethyl 3-chloro-3-oxopropionate (20.7 ml, 162 mmol), and the mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into ice water and the precipitated crystals were collected by filtration. These were washed with water and diisopropyl ether in sequence and then air-dried, thereby obtaining 37.1 g of title compound as yellow powder. Yield 88%.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washThese were washed with water and diisopropyl ether in sequence
  3. customair-dried

Sources & evidence

ORD record
ord-3bd1ab7def6a434fba1f6a5fd162598c
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

Loading…