4-Nitrobenzoyl chloride → 1-(4-Nitrobenzoyl)-amino-2-[2-(4-nitrobenzoyloxymethyl)phenyl]ethane

HRID 1156887Notes

Reaction equation

HRID 1156887 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][OH:11].[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]>N1C=CC=CC=1>[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([CH:2]([NH2:1])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:10][O:11][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 12832783[2-(2-Aminoethyl)phenyl]methanol

Product 1

HCID 205339201-(4-Nitrobenzoyl)-amino-2-[2-(4-nitrobenzoyloxymethyl)phenyl]ethaneYield 80.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Amino-2-(2-hydroxymethylphenyl)ethane (10.2 g) was dissolved in 40 ml of pyridine, and with stirring under ice cooling, 25 g of 4-nitrobenzoyl chloride was added gradually. The mixture was stirred at room temperature for 4 hours and then at 50° C. for 1 hour, and poured into ice water. The crystals precipitated were washed in water, dried, and recrystallized from tetrahydrofuran-benzene to afford 24.3 g of 1-(4-nitrobenzoyl)-amino-2-[2-(4-nitrobenzoyloxymethyl)phenyl]ethane having a melting point of 168.2° to 169.7° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. customThe crystals precipitated
  3. washwere washed in water
  4. customdried
  5. customrecrystallized from tetrahydrofuran-benzene

Sources & evidence

ORD record
ord-6cd491ef725e492c98c732c8f496e55a
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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