Benzylamine → 1-Benzyl-3-phenylurea

HRID 1112332Notes

Reaction equation

HRID 1112332 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([NH:15][C:16](OC2C(O)=C(C3C=CC=CC=3)S(=O)(=O)C=2C2C=CC=CC=2)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OCC)(=O)C>[CH2:1]([NH:8][C:16]([NH:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 227636553-(Phenylcarbamyloxy)-4-hydroxy-2,5-diphenylthiophene-1,1-dioxide

Product 1

HCID 2803631-Benzyl-3-phenylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

540 mg of benzylamine are added to 2.1 g of 3-(N-phenylcarbamyloxy)-4-hydroxy-2,5-diphenylthiophene-1,1-dioxide in 20 ml of ethyl acetate. The solution is boiled under reflux for 1 hour and then washed three times with 25 ml of concentrated aqueous NaHCO3 solution and three times with 20% strength aqueous citric acid solution. The wash liquors are extracted with ethyl acetate and the combined organic phases are dried over magnesium sulfate. After evaporating the filtrate, the crystalline residue is recrystallized from dilute ethanol.

Workup

  1. temperatureunder reflux for 1 hour
  2. washwashed three times with 25 ml of concentrated aqueous NaHCO3 solution and three times with 20% strength aqueous citric acid solution
  3. extractionThe wash liquors are extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried over magnesium sulfate
  5. customAfter evaporating the filtrate
  6. customthe crystalline residue is recrystallized from dilute ethanol

Sources & evidence

ORD record
ord-195cfb6f7ac3451089078aa7bd2aced2
Source dataset
uspto-grants-1978_10
Patent number
US04122090

Reaction notes

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