Dimethylformamide → HCID 14500944, compound

HRID 1032618Notes

Reaction equation

HRID 1032618 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.[H-].[Na+].[CH3:21][C:22]1([CH3:45])[CH2:27][CH2:26][C:25]2[CH:28]=[C:29]([CH2:32][CH2:33]C3C=C(C)C=CC=3S([O-])(=O)=O)[CH:30]=[CH:31][C:24]=2[O:23]1>O>[CH3:21][C:22]1([CH3:45])[CH2:27][CH2:26][C:25]2[CH:28]=[C:29]([CH2:32][CH2:33][O:1][C:2]3[CH:3]=[C:4]([NH:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=3)[CH:30]=[CH:31][C:24]=2[O:23]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 785621,1-DIME-3-(3-HYDROXYPHENYL)UREAHCID 86744229HCID 86744229, compound

Product 1

HCID 14500944HCID 14500944, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.8 g of 1-(3-hydroxyphenyl)-3,3-dimethylurea was dissolved into 20 ml of dried N,N-dimethylformamide, and 0.4 g of 60% sodium hydride was added thereto. After the mixture was stirred for 15 minutes, 3.6 g of 3-[(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-p-toluene sulfonate was added dropwise thereto under cooling with ice. After the mixture was stirred at room temperature for 5 hours, it was poured into iced water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous sodium sulfate and ethyl acetate was distilled off. The residue was purified by silica gel column chromatography using n-hexane/ethyl acetate (1/1) as a developer to obtain 2.4 g of Compound No. 94 shown in Table 5.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringAfter the mixture was stirred at room temperature for 5 hours
  4. extractionextracted with ethyl acetate
  5. washAfter the organic layer was washed with water, it
  6. dry with materialwas dried over anhydrous sodium sulfate and ethyl acetate
  7. distillationwas distilled off
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9697774c29b44b4991aa57f26c65ec72
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

Loading…