Water → 4-n-Propylphenylurea

HRID 344658Notes

Reaction equation

HRID 344658 reaction equation
[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH2:2][CH3:3].O.[N-:12]=[C:13]=[O:14].[Na+]>C(O)(=O)C>[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:13]([NH2:12])=[O:14])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 759084-PropylanilineHCID 11051568NaNCO

Product 1

HCID 142764214-n-PropylphenylureaYield 93.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 31.4 g of p-n-propylaniline dissolved in 116 ml of acetic acid and 232 ml of water was added dropwise into 200 ml of a mixed solution comprising 130 g of sodium isocyanate and 900 ml of water, and then stirred in an ice-bath for 30 minutes. The crystals precipitated were filtered, washed with water and dried to give 38.88 g of 4-n-propylphenylurea. After the 4-n-propylphenylurea was added in portions into 107.6 ml of 20% fuming sulfuric acid, the reaction was carried out at 60° C. for 2 hours. Under cooling in an ice-bath, about 400 ml of ice was added into the reaction mixture, followed by heating under reflux for 4 hours. The crystals precipitated by cooling were filtered, washed with water and then dried to give 30.09 g of the above title product (yield: 64.1%). Melting point: 30 261.7°-262.3° C.

Workup

  1. customThe crystals precipitated
  2. filtrationwere filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-72f6fb7c948e4631a3af516985e5cd09
Source dataset
uspto-grants-1991_10
Patent number
US05053409

Reaction notes

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