Ammonia → HCID 13828992, compound

HRID 1634694Notes

Reaction equation

HRID 1634694 reaction equation
N(CC[C:6]1[C:7](=O)[NH:8][C:9](=[O:12])[NH:10][CH:11]=1)=[N+]=[N-].[CH:14](Cl)(Cl)Cl.[CH3:18][OH:19].[NH3:20]>N1C=CC=CC=1>[NH2:20][CH2:14][CH2:11][N:10]1[C:18](=[O:19])[CH:6]=[CH:7][NH:8][C:9]1=[O:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 15408026HCID 15408026, compoundHCID 21584188Chloroform methanol

Product 1

HCID 13828992HCID 13828992, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

14.2 g (78.0 mmol) of 30 were suspended in 175 ml of pyridine in a 250 ml three-necked flask equipped with an internal thermometer and reflux condenser and the mixture was treated with 61.4 g (234 mmol) of triphenylphosphine2). It was heated at 60° C. for 5 hours and stirred overnight at room temp. (TLC checking, CHCl3/MeOH 5:1). 40 ml of 25% strength ammonia solution were added to the suspension, which then clarified. The solvents were removed in vacuo in a rotary evaporator. The residue was stirred at room temp. for 30 min in 200 ml of CH2Cl2/MeOH 1:1, and the recipitate was filtered off and washed with CH2Cl2. After drying in vacuo in a desiccator over phosphorus entoxide, 10.0 g (85%) of 31 of m.p. 214-220° C. were obtained.

Workup

  1. customequipped with an internal thermometer
  2. temperaturereflux condenser
  3. additionthe mixture was treated with 61.4 g (234 mmol) of triphenylphosphine2)
  4. customThe solvents were removed in vacuo in a rotary evaporator
  5. filtrationthe recipitate was filtered off
  6. washwashed with CH2Cl2
  7. dry with materialAfter drying in vacuo in a desiccator over phosphorus entoxide

Sources & evidence

ORD record
ord-6f5a7967b87a4a2bbaa6c09408b71df7
Source dataset
uspto-grants-2003_01
Patent number
US06506896B1

Reaction notes

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