2,3-Dihydro-6-methoxy-2-methyl-4-benzofuranamine → N-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)diacetamide

HRID 614007Notes

Reaction equation

HRID 614007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:9][CH:8]([CH3:10])[CH2:7][C:6]2=[C:11]([NH2:13])[CH:12]=1>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:13]([C:8]([CH3:7])=[O:9])[C:3](=[O:2])[CH3:12])[C:6]2[CH2:7][CH:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 213298112,3-Dihydro-6-methoxy-2-methyl-4-benzofuranamine

Product 1

HCID 70600751N-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)diacetamide

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A reaction mixture consisting of 2.4 grams of 2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine, 10 cc of acetic anhydride and one drop of pyridine is heated to 130°-140° C. for 90 minutes. After cooling and evaporating the excess of acetic anhydride, the residue is distilled under reduced pressure yielding 2.4 grams (69 percent of theoretical) of the compound of the title. B.p./0.4 mmHg 160° C. The distillate which solidifies is crystallized from ethyl ether-petroleum ether. M.p. 56°-57° C.

Workup

  1. temperatureis heated to 130°-140° C. for 90 minutes
  2. temperatureAfter cooling
  3. customevaporating the excess of acetic anhydride
  4. distillationthe residue is distilled under reduced pressure
  5. customyielding 2.4 grams (69 percent of theoretical) of the compound of the title
  6. custom0.4 mmHg 160° C
  7. customThe distillate which solidifies is crystallized from ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-109f9c69e96e4ba9bacf569adf6d7e82
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

Loading…