Toluene → 1-(2,4-dinitrophenyl)urea

HRID 1447322Notes

Reaction equation

HRID 1447322 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C1(C)C=CC=CC=1.ClS([N:25]=[C:26]=[O:27])(=O)=O>O>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH:6][C:26]([NH2:25])=[O:27])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73212,4-DinitroanilineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 37767081-(2,4-dinitrophenyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

311 Parts of 2,4-dinitroaniline are stirred in 2600 parts of toluene with 312 parts of chlorosulfonyl isocyanate for 4hours at 80° C. At 25° C., 360 parts of water are added to the resulting suspension of N-2,4-dinitrophenyl- N'-chlorosulfonyl urea without intermediate isolation of the latter, and the mixture obtained is saponified at 60° C. within 4 hours to yield 2,4-dinitrophenyl urea. After diluting it with water, the mixture is filtered, while hot, and the product is washed with hot toluene and water. After drying in vacuo, there are obtained 347 parts of 2,4-dinitrophenyl urea having a melting point of from 195° to 197° C.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-fd1f318532c1425f9e3775869cc901b2
Source dataset
uspto-grants-1982_02
Patent number
US04316861

Reaction notes

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