Dimethylformamide → 1-[4-(2,3-Dihydro-2,2-dimethyl-6-benzofuranylmethyloxy)phenyl]-3-methoxy-3-methylurea

HRID 1032606Notes

Reaction equation

HRID 1032606 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)=[CH:10][C:4]=2[O:3]1.CN(C)C=O.C(N(CC)CC)C.[CH3:33][O:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>O>[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH:17][C:36]([N:35]([O:34][CH3:33])[CH3:39])=[O:37])=[CH:15][CH:14]=3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 221645334-(2,3-Dihydro-2,2-dimethyl-6-benzofuranylmethyloxy)aniline

Product 1

HCID 144998691-[4-(2,3-Dihydro-2,2-dimethyl-6-benzofuranylmethyloxy)phenyl]-3-methoxy-3-methylureaYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.9 g of 4-(2,3-dihydro-2,2-dimethyl-6-benzofuranylmethyloxy)aniline was dissolved into 70 ml of N,N-dimethylformamide, and 2.8 g of triethylamine was added thereto. 3.8 g of N-methoxy-N-methylcarbamoyl chloride was slowly added dropwise thereto. After the mixture was stirred at room temperature, 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. Ethyl acetate was distilled off and the residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/2) as a developer to obtain 6.0 g of Compound No. 4 shown in Table 1.

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
  5. distillationEthyl acetate was distilled off

Sources & evidence

ORD record
ord-61e3415f67074570a9d5168039f43998
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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