N-methoxy-N-methylcarbamoyl chloride → HCID 14499857, compound

HRID 1032610Notes

Reaction equation

HRID 1032610 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][O:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1>[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:23]([N:22]([O:21][CH3:20])[CH3:26])=[O:24])=[CH:15][CH:14]=3)[CH:9]=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 14998275HCID 14998275, compound

Product 1

HCID 14499857HCID 14499857, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.5 g of 4-(2,3-dihydro-2-methyl-5-benzofuranylmethyloxy)aniline was dissolved into 30 ml of pyridine, and 3.8 g of N-methoxy-N-methylcarbamoyl chloride was slowly added dropwise thereto under cooling with ice. After 2-hours' continuous stirring, pyridine was distilled off under a reduced pressure, and the residual oily matter was dissolved into 100 ml of toluene. After the reaction mixture was subsequently washed with water, diluted hydrochloric acid and saturated sodium chloride aqueous solution, toluene was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 7.3 g of Compound No. 40 shown in Table 2.

Workup

  1. additionwas slowly added dropwise
  2. temperatureunder cooling with ice
  3. distillationAfter 2-hours' continuous stirring, pyridine was distilled off under a reduced pressure
  4. dissolutionthe residual oily matter was dissolved into 100 ml of toluene
  5. washAfter the reaction mixture was subsequently washed with water, diluted hydrochloric acid and saturated sodium chloride aqueous solution, toluene
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-27128ad2f4bd4d0da9f437fa6cd9b9ec
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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