N-methoxy-N-methylcarbamoyl chloride → HCID 14011465, compound

HRID 246990Notes

Reaction equation

HRID 246990 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[C:4]=2[O:3]1.[CH3:20][O:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>CN(C)C=O>[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH:16][C:23]([N:22]([O:21][CH3:20])[CH3:26])=[O:24])=[CH:14][CH:13]=3)[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 143072814-(2,3-Dihydro-2,2-dimethyl-7-benzofuranyloxy)aniline

Product 1

HCID 14011465HCID 14011465, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of 4-(2,3-dihydro-2,2-dimethyl-7-benzofuranyloxy)aniline was dissolved in 20 ml of N,N-dimethylformamide, and 0.8 g of N-methoxy-N-methylcarbamoyl chloride was gradually added to this solution at room temperature. After 1.5 hours, N,N-dimethylformamide was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and dried over magnesium sulfate. After distilling off the solvent, the residual oily substance was purified by silica gel column chromatography by using a solvent mixture of ethyl acetate/n-hexane=1/4 as the developer, to obtain 1.4 g of compound No. 2 as identified in Table 1.

Workup

  1. distillationN,N-dimethylformamide was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residual oily substance was purified by silica gel column chromatography
  7. additiona solvent mixture of ethyl acetate/n-hexane=1/4 as the developer

Sources & evidence

ORD record
ord-1648f5ded9084abaa807a50324845690
Source dataset
uspto-grants-1987_11
Patent number
US04705554

Reaction notes

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