Dimethylformamide → HCID 14499852, compound

HRID 1032611Notes

Reaction equation

HRID 1032611 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)[CH:9]=[CH:10][C:4]=2[O:3]1.[CH3:20][N:21]([CH3:24])[CH:22]=[O:23].C(N(CC)CC)C.CN(C)C(Cl)=O>O>[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH:17][C:22]([N:21]([CH3:24])[CH3:20])=[O:23])=[CH:15][CH:14]=3)[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 14998275HCID 14998275, compound

Product 1

HCID 14499852HCID 14499852, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.5 g of 4-(2,3-dihydro-2-methyl-5-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,N-dimethylcarbamoyl 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 and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (2/1) as a developer to obtain 5.8 g of Compound No. 41 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. distillationwas distilled off

Sources & evidence

ORD record
ord-e48bee924321465c97acd96e4a937ee7
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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