N-methoxy-N-methylcarbamoyl chloride → HCID 14499867, compound

HRID 1032605Notes

Reaction equation

HRID 1032605 reaction equation
[CH3:1][C:2]1([CH3:20])[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.[CH3:21][O:22][N:23]([CH3:27])[C:24](Cl)=[O:25]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:20])[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:24]([N:23]([O:22][CH3:21])[CH3:27])=[O:25])=[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 14998268HCID 14998268, compound

Product 1

HCID 14499867HCID 14499867, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.9 g of 4-(2,3-dihydro-2,2-dimethyl-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 solution 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 (1/3) as a developing solvent (developer) to obtain 7.6 g of Compound No. 2 shown in Table 1.

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 solution was subsequently washed with water, diluted hydrochloric acid and saturated sodium chloride aqueous solution, toluene
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-cc6fc15888f24ebda846bae4c192a658
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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