Dimethylformamide → HCID 12942108, compound

HRID 848225Notes

Reaction equation

HRID 848225 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F-].[K+].CN(C=O)C.[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH:22]=[CH:23][C:24]=1[OH:25]>O>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27](=[O:31])[N:28]([CH3:29])[CH3:30])[CH:22]=[CH:23][C:24]=1[O:25][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 107572-ChloroacetophenoneHCID 182205N'-(3-Chloro-4-hydroxyphenyl)-N,N-dimethylcarbamimidic acidHCID 522689Potassium Fluoride

Product 1

HCID 12942108HCID 12942108, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of α-chloroacetophenone (4,64 g; 0.03 mol), anhydrous potassium fluoride and DMF (200 ml) is stirred for 15 minutes. Next, 3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea (6.44 g; 0.03 mol) is added and the mixture stirred for 20 hours at room temperature and then for 24 hours at 80° C. The mixture is then drowned in water, and extracted with methylene chloride. The organic layer is separated, washed with water and filtered through a 5 cm pad of neutral alumina. The pad is washed with acetonitrile, filtrate and washings are combined and evaporated under vacuum to give a brown-yellow oil (7.0 g, 70.1%). This oil is purified by chromatographing on silica gel (eluent: methylene chloride) to afford the title compound: 6.75 g of a cream colored solid, m.p. 148°-150° C.

Workup

  1. stirringthe mixture stirred for 20 hours at room temperature
  2. waitfor 24 hours at 80° C
  3. extractionextracted with methylene chloride
  4. customThe organic layer is separated
  5. washwashed with water
  6. filtrationfiltered through a 5 cm pad of neutral alumina
  7. washThe pad is washed with acetonitrile, filtrate and washings
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-9444211ec20445109c9eed35250ef900
Source dataset
uspto-grants-1981_10
Patent number
US04294986

Reaction notes

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