Hydrochloric Acid → Ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate

HRID 606490Notes

Reaction equation

HRID 606490 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.Cl[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>C1COCC1>[NH2:6][C:4]([C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[NH:1][C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 976652-Amino-5-nitrobenzamide

Product 1

HCID 12264866Ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetateYield 28.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-5-nitrobenzamide (18.1 g) and triethylamine (15 mL) in THF (100 mL) was added dropwise a solution of ethyl chloroglyoxylate (14.4 g) in THF (20 mL) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and saturated brine, dried, and concentrated. The obtained crude crystals were washed with diisopropyl ether to give ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate (8.1 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe obtained crude crystals
  7. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-83230ef2c99740ea96d4df91289be64d
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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