Aniline → Triphenylurea

HRID 2291599Notes

Reaction equation

HRID 2291599 reaction equation
[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:24]1([NH2:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[C:24]1([NH:30][C:8](=[O:9])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chloride

Product 1

HCID 597994Triphenylurea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Diphenylcarbamic chloride (23 g, 0.1 mol, Aldrich Chemical Co., Milwaukee, Wis., U.S.A.) was added to a solution of 10.1 g of triethylamine and 9.3 g (0.1 mol) of benzeneamine in 150 ml of chloroform. The resulting solution was heated under reflux overnight. The solution was cooled to room temperature and washed three times with 100-ml portions of brine solution, dried over anhydrous magnesium sulfate, and evaporated to give an off-white solid which was triturated with diethyl ether to give triphenylurea as a white solid, mp 136°-138° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux overnight
  3. washwashed three times with 100-ml portions of brine solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto give an off-white solid which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-d0da4c46074645c0b6ec3f4518e0b394
Source dataset
uspto-grants-1989_01
Patent number
US04797419

Reaction notes

Loading…