Ammonium Acetate → HCID 13207875, compound

HRID 918249Notes

Reaction equation

HRID 918249 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][N:9]([C:16]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:17]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)[C:10](=[O:15])C(Cl)(Cl)Cl.C([O-])(=O)C.[NH4+:37]>C(O)(C)(C)C>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][N:9]1[C:16]2[C:17](=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:37][C:10]1=[O:15]

Participants

4

Reactant 2

HCID 517165Ammonium Acetate2×HCID 54358427HCID 54358427, compound

Product 1

HCID 13207875HCID 13207875, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2.5 g of 2-[ N-(2-norbornylmethyl)trichloroacetamido]-5-nitrobenzophenone in 50 ml of tert-butyl alcohol was added 2 g of ammonium acetate and the resulting mixture was heated under reflux for 7 hours. Then 2 g of ammonium acetate was added thereto and the reaction was continued for additional 8 hours. The solvent was removed under reduced pressure, and the residue was extracted with chloroform. The chloroform extract was washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness. The residual oil was crystallized from a mixture of carbon tetrachloride and diethyl ether to give 1-(2-norbornylmethyl)-4-phenyl-6-nitro-2(1H)-quinazolinone, m.p. 160°C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 7 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness
  9. customThe residual oil was crystallized from a mixture of carbon tetrachloride and diethyl ether

Sources & evidence

ORD record
ord-8f1e1147a88e41e3ae2d089d948350a5
Source dataset
uspto-grants-1976_07
Patent number
US03970654

Reaction notes

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