Aniline → Urea, 1,1-diethyl-3-phenyl-

HRID 1112329Notes

Reaction equation

HRID 1112329 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([NH:10][CH2:11][CH3:12])[CH3:9].[O:13]1CCC[CH2:14]1>>[CH2:8]([N:10]([CH2:11][CH3:12])[C:14]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13])[CH3:9]

Participants

4

Reactant 3

HCID 6115AnilineHCID 8021DiethylamineHCID 8028Tetrahydrofuran

Product 1

HCID 13906Urea, 1,1-diethyl-3-phenyl-

Procedure

0.93 g of aniline is added to 3.26 g of 2,4-carbonyldioxy-2,5-diphenylthiophene-1,1-dioxide in 25 ml of dry tetrahydrofuran. The mixture is left to stand for 30 minutes at 20° C., 0.73 g of diethylamine is added and the mixture is left to stand for a further 40 minutes. After distilling off the tetrahydrofuran, the residue is taken up in chloroform and the chloroform solution is washed successively with aqueous 1N hydrochloric acid and twice with aqueous sodium carbonate solution and water. After drying over magnesium sulfate and evaporating under reduced pressure, 1.4 g of slightly yellowish crystals which, as the crude product, have a melting point of 81°-85° C. (melting point quoted in the literature of 85° C.) remain.

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. waitto stand for a further 40 minutes
  4. distillationAfter distilling off the tetrahydrofuran
  5. washthe chloroform solution is washed successively with aqueous 1N hydrochloric acid and twice with aqueous sodium carbonate solution and water
  6. dry with materialAfter drying over magnesium sulfate
  7. customevaporating under reduced pressure, 1.4 g of slightly yellowish crystals which, as the crude product
  8. customquoted in the literature of 85° C.

Sources & evidence

ORD record
ord-f182a290e25b47db9f38349fa195e536
Source dataset
uspto-grants-1978_10
Patent number
US04122090

Reaction notes

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