HCID 23085720, compound → HCID 178526438, compound

HRID 2243094Notes

Reaction equation

HRID 2243094 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[NH2:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[C:2]1([C:1]2[NH:9][CH2:10][C:11]3[C:12](=[CH:13][CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=3)[N:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 23085720HCID 23085720, compound

Product 1

HCID 178526438HCID 178526438, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

N-Benzoyl-2-amino-5-nitrobenzylamine (33 g, 0.12 mol) and phosphoryl chloride (150 ml) are refluxed for 3 hours. The mixture is concentrated and water is added, followed by addition of aqueous ammonia (pH>10). The product is filtered off and recrystallized from water, and then from 2/1 isopropyl ether/hexane. Yield: 27.6 g (89%); IR (KBr): 3387, 3198, 1599, 1512, 1341 cm−1; 1H-NMR (d6-DMSO) 7.95 (m, 4H); 7.30 (m, 4H); 7.01 (m, 1H); 4.71 (s, 2H).

Workup

  1. concentrationThe mixture is concentrated
  2. additionwater is added
  3. additionfollowed by addition of aqueous ammonia (pH>10)
  4. filtrationThe product is filtered off
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-5ad2afaa75154c17b86dc788fb69ae67
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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