Ethanol → HCID 22387919, compound

HRID 1072838Notes

Reaction equation

HRID 1072838 reaction equation
C(O)C.O1CCCC1.[Cl:9][C:10]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:11]=1[CH2:12][NH:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:25][C:24]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[NH:13][CH2:12][C:11]1[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:10]=1[Cl:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 22388272HCID 22388272, compound

Product 1

HCID 22387919HCID 22387919, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethanol (7 ml), tetrahydrofuran (7 ml) and water (28 ml) were added to ethyl 3-(2,4-dichlorobenzylamino)-4-nitrobenzoate (1.40 g), and sodium hydrosulfite (4.50 g) was added at room temperature. The mixture was stirred at 50° C. for 20 min. The reaction mixture was extracted with chloroform and water, and the organic layer was washed with saturated brine, dried and concentrated to give the objective compound (1.4 g, as a crude product). The crude product was used in the following reaction as it was.

Workup

  1. additionwas added at room temperature
  2. extractionThe reaction mixture was extracted with chloroform and water
  3. washthe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the objective compound (1.4 g

Sources & evidence

ORD record
ord-3f100d329dd040888504ad5ced33f16f
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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