Water → HCID 22033802, compound

HRID 2163519Notes

Reaction equation

HRID 2163519 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:15]1([N:21]=[C:22]=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1C=CC=CC=1>[C:1]([CH:4]([C:5](=[O:7])[CH3:6])[C:22]([NH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 31261Acetylacetone

Product 1

HCID 22033802HCID 22033802, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of acetylacetone (5 g) and triethylamine (5.2 g) in dry benzene (50 ml) was treated with phenyl isocyanate (6 g) in dry benzene (25 ml). The mixture was stirred for 3 hr at room temperature. Water (50 ml) was then added, the mixture shaken and the water layer separated. The benzene solution was extracted with two further portions (25 ml) of water and the combined aqueous extracts acidified with dilute hydrochloric acid. The product precipitated and was collected by filtration, washed with water and dried. Diacetyl acetanilide (7.0 g, 73%) was obtained as a colourless solid, m.p. 119-121° C.

Workup

  1. stirringthe mixture shaken
  2. customthe water layer separated
  3. extractionThe benzene solution was extracted with two further portions (25 ml) of water
  4. customThe product precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f461f0e1bcd84d2082fefe54d3d0ce03
Source dataset
uspto-grants-1979_01
Patent number
US04134987

Reaction notes

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