Phenylurea → HCID 15557216, compound

HRID 1763845Notes

Reaction equation

HRID 1763845 reaction equation
C1(N[C:8]([NH:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[N:13][C:12]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:9])C=CC=CC=1.C1(NC(N)=O)C=CC=CC=1>C(OCC)(=O)C.C(OCC)C>[C:19]1([CH3:22])[CH:20]=[CH:21][C:16]([C:14]2[S:15][C:11]3[NH:10][C:8](=[O:9])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:12]=3[N:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 15557213HCID 15557213, compound

Product 1

HCID 15557216HCID 15557216, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

To a solution of 1.33 g (5 millimole) of 5-amino-2-(p-tolyl)-4-phenylthiazole in 45 ml of benzene, 0.9 g (7.5 millimole) of the phenylisocyanate in 5 ml of anhydrous benzene is added at room temperature. The reaction mixture is refluxed for 3 hours and 0.45 g (3.75 millimole) of additional phenylisocyanate is added, refluxing is continued for an additional 3 hours, the reaction mixture is cooled and the insoluble part recovered by filtration under vaccum and washed with benzene. On crystallization from ethanol, 1.5 g of the corresponding phenylurea is obtained (M.p. 247°-263° C.; yield 78%). 25 Grams of the resulting 1-phenyl-3-[4-phenyl-2-(p-tolyl)-thiazol-5-yl]urea is heated on a metal bath to a temperature of 300°-305° C.; until aniline distills which, on condensing, dissolves phenylurea which has previously sublimed. After some minutes, the reaction mass is cooled and ethyl acetate-ethyl ether mixture is added thereto. On filtering under vacuum, a substance is recovered which, on crystallization from dimethylformamide, gives 19 g of the desired product (m.p. 314°-316° C.; yield 75%).

Workup

  1. distillationuntil aniline distills which
  2. customon condensing
  3. waitAfter some minutes
  4. temperaturethe reaction mass is cooled
  5. filtrationOn filtering under vacuum
  6. customa substance is recovered which
  7. customon crystallization from dimethylformamide

Sources & evidence

ORD record
ord-4668c4d93806404b8e97445c5e81a0fc
Source dataset
uspto-grants-1978_09
Patent number
US04113731

Reaction notes

Loading…