Chloral → HCID 13341913, compound

HRID 2286848Notes

Reaction equation

HRID 2286848 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].O=[CH:15][C:16]([Cl:19])([Cl:18])[Cl:17]>>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:13][CH:15]([C:16]([Cl:19])([Cl:18])[Cl:17])[NH:11][C:9]2=[O:10])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 6407ChloralHCID 976652-Amino-5-nitrobenzamide2×

Product 1

HCID 13341913HCID 13341913, compound

Procedure

5-Nitroanthranilamide (6.5 g.) and anhydrous chloral (65 ml.) were stirred together at ambient temperature, until thin layer chromatography indicated that all the 5-nitroanthranilamide had disappeared (6 days). The excess of chloral was distilled off, and the resulting syrup was heated with concentrated sulphuric acid (125 ml.) on a steam bath for 10 minutes. The reaction mixture was cooled and poured into ice/water (1 kg.), and the solid product which was precipitated was filtered off, washed with water (3×200 ml.) and crystallised from ethanol (450 ml.) to give 1,2-dihydro-6-nitro-2-trichloromethylquinazolin-4-one, m.p. 278°-280° C.

Workup

  1. custom(6 days)
  2. distillationThe excess of chloral was distilled off
  3. temperaturethe resulting syrup was heated with concentrated sulphuric acid (125 ml.) on a steam bath for 10 minutes
  4. temperatureThe reaction mixture was cooled
  5. additionpoured into ice/water (1 kg.)
  6. customthe solid product which was precipitated
  7. filtrationwas filtered off
  8. washwashed with water (3×200 ml.)
  9. customcrystallised from ethanol (450 ml.)

Sources & evidence

ORD record
ord-06cc520a664145da830e9c4d00d86ce8
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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