Dimethylformamide → HCID 14499863, compound

HRID 1032613Notes

Reaction equation

HRID 1032613 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11]Cl)[CH:9]=[CH:10][C:4]=2[O:3]1.[OH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]([N:23]([O:25][CH3:26])[CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11][O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21]([N:23]([O:25][CH3:26])[CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=3)[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14998277HCID 14998277, compoundHCID 15565623N'-(3-Hydroxyphenyl)-N-methoxy-N-methylurea

Product 1

HCID 14499863HCID 14499863, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2.8 g of 2,3-dihydro-2-methyl-5-benzofuranylmethyl chloride and 3.0 g of 1-(3-hydroxyphenyl)-3-methoxy-3-methylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was dried off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/2) as a developer to obtain 3.7 g of Compound No. 46 shown in Table 2.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water, it
  4. dry with materialwas dried over anhydrous magnesium sulfate and ethyl acetate
  5. customwas dried off

Sources & evidence

ORD record
ord-df8930bdfd4d4b5d86c13ecf03c1c006
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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