Acetic Acid → HCID 23468860, compound

HRID 128308Notes

Reaction equation

HRID 128308 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[C:10]([CH:12]3[CH2:18][C:17](=[O:19])[O:16][C:14](=O)[CH2:13]3)[CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH:20]1([NH2:23])[CH2:22][CH2:21]1.C(O)(=O)C.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:20]1([N:23]2[C:14](=[O:16])[CH2:13][CH:12]([C:10]3[CH:9]=[CH:8][C:5]4[C:6]([CH3:7])=[C:2]([CH3:1])[O:3][C:4]=4[CH:11]=3)[CH2:18][C:17]2=[O:19])[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 69828CyclopropylamineHCID 53815846HCID 53815846, compound

Product 1

HCID 23468860HCID 23468860, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.58 g (0.01 mol) of 3-(2,3-dimethyl-6-benzofuranyl)-glutaric anhydride (c.f. Example (4c), 0.855 g, corresponding to about 1.04 ml (1.5 molar equivalents) of cyclopropylamine and 11 ml of glacial acetic acid are dissolved in 11 ml of toluene and the solution is refluxed for 2 days using a water separator. The reaction mixture is then cooled to room temperature, diluted with 50 ml of ethyl acetate and washed twice with 25 ml of water. Thereafter, the organic phase is extracted with 2 N aqueous sodium carbonate solution to remove the acid constituents, then washed again with water and with saturated sodium chloride solution (25 ml of each) and dried over sodium sulfate and the ethyl acetate is evaporated off under a waterpump vacuum. A sand-coloured crude product of melting point 180°-182° is thereby obtained. This is recrystallised from warm methylene chloride and hexane, whereupon N-cyclopropyl-3-(2,3-dimethyl-6-benzofuranyl)-glutarimide is obtained as white flakes of melting point 183°-184° .

Workup

  1. temperaturethe solution is refluxed for 2 days
  2. washwashed twice with 25 ml of water
  3. extractionThereafter, the organic phase is extracted with 2 N aqueous sodium carbonate solution
  4. customto remove the acid constituents
  5. washwashed again with water and with saturated sodium chloride solution (25 ml of each) and
  6. dry with materialdried over sodium sulfate
  7. customthe ethyl acetate is evaporated off under a waterpump vacuum
  8. customA sand-coloured crude product of melting point 180°-182° is thereby obtained
  9. customThis is recrystallised
  10. temperaturefrom warm methylene chloride and hexane

Sources & evidence

ORD record
ord-fb2d515991ac40fcbe35bd24ec073218
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

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