4-Nitroaniline → Methyl-3-(p-nitrophenylcarbamoyl)benzoate

HRID 232392Notes

Reaction equation

HRID 232392 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19])([O:13][CH3:14])=[O:12]>CC(N(C)C)=O.N1C=CC=CC=1>[CH3:14][O:13][C:11](=[O:12])[C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](=[O:19])[NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:16]=1

Participants

5

Reactant 2

HCID 74754-NitroanilineHCID 15563901Methyl 3-(chlorocarbonyl)benzoate

Product 1

HCID 17175216Methyl-3-(p-nitrophenylcarbamoyl)benzoateYield 97.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31374DimethylacetamideSolvent2×

Procedure

In a 1-liter 3-necked flask fitted with an inlet tube for nitrogen, a magnetic stirrer, a dropping funnel and a thermometer there were introduced 76 g (0.5 moles) of p-nitroaniline in 600 ml of dimethylacetamide and 80 ml of pyridine. (Both solvents had previously been dried over a molecular sieve 3A). Over a period of 45 minutes 99.2 g (0.5 moles) of 3-carbomethoxybenzoyl chloride in 100 ml of dimethylacetamide were added with stirring and cooling, care being taken that the temperature did not rise to above 15° C. In the process a yellow precipitate was formed. After all the ingredients had been added, stirring was continued for 1 more hour at 20° C. The reaction mixture was poured into 2 l of ice water, filtered, washed 6 times with water and finally with methanol. After drying at 70° C. and a pressure of 133 Pa 146 g of the envisaged product were obtained in a yield of 97%. The melting point was 206°-207.6° C. In an analogous manner there were prepared:

Workup

  1. customIn a 1-liter 3-necked flask fitted with an inlet tube for nitrogen, a magnetic stirrer, a dropping funnel
  2. dry with material(Both solvents had previously been dried over a molecular sieve 3A)
  3. temperaturecooling
  4. customdid not rise to above 15° C
  5. customIn the process a yellow precipitate was formed
  6. additionAfter all the ingredients had been added
  7. stirringstirring
  8. customwas continued for 1 more hour at 20° C
  9. filtrationfiltered
  10. washwashed 6 times with water
  11. customAfter drying at 70° C.

Sources & evidence

ORD record
ord-87a3edaeb4bc434ea9f5d59cd7ad7010
Source dataset
uspto-grants-1989_07
Patent number
US04851562

Reaction notes

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