Water → 2,4,6-Trinitroaniline

HRID 1828384Notes

Reaction equation

HRID 1828384 reaction equation
[C:1]1([C:15]([O-])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=[C:6]([N+:7]([O-:9])=[O:8])[CH:5]=1)[N+:2]([O-:4])=[O:3].[NH4+].C(=O)([O-])[NH2:19].[NH4+].O>S1(CCCC1)(=O)=O>[CH:5]1[C:1]([N+:2]([O-:4])=[O:3])=[C:15]([NH2:19])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]=1[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 8577Ammonium picrateHCID 517232Ammonium Carbamate

Product 1

HCID 102712,4,6-TrinitroanilineYield 88.9%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

Ammonium picrate (0.92 g, 3.7 mmol) and ammonium carbamate (0.59 g, 7.5 mmol) are suspended in sulfolane (3 ml) and stirred for 2 hr with the temperature of the reaction increasing from 25° C. to 177° C. The reaction is continued an additional 6 hr at 177° C. and cooled to ambient temperature. Water (30 ml) is added to the slurry and the product is collected, washed with water and dried to yield 0.75 g (87%) of picramide (Table 1, entry 4).

Workup

  1. temperatureincreasing from 25° C. to 177° C
  2. waitThe reaction is continued an additional 6 hr at 177° C.
  3. customthe product is collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-abf3f2469a3247ab997cfedc77941cfb
Source dataset
uspto-grants-2006_06
Patent number
US07057072B2

Reaction notes

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