Water → HCID 23468914, compound

HRID 128299Notes

Reaction equation

HRID 128299 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[C:14](=[O:15])[CH2:13]3)[CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH3:20][NH2:21].O>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:20][N:21]1[C:17](=[O:19])[CH2:18][CH:12]([C:10]2[CH:9]=[CH:8][C:5]3[C:6]([CH3:7])=[C:2]([CH3:1])[O:3][C:4]=3[CH:11]=2)[CH2:13][C:14]1=[O:15]

Participants

6

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 53815846HCID 53815846, compound

Product 1

HCID 23468914HCID 23468914, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent2×

Procedure

3.87 g (0.015 mol) of 3-(2,3-dimethyl-6-benzofuranyl)-glutaric anhydride [c.f. Example (4a) to (e)] are dissolved in 12.5 ml of toluene and 12.5 ml of glacial acetic acid. 10 ml of a 1.88 molar solution of methylamine in toluene are added to this solution at room temperature and the reaction mixture is heated to the boiling point for 61/2 hours, using a water separator. The cooled reaction mixture is poured onto an ice-water mixture and extracted with ether and the organic phase is washed with sodium bicarbonate and saturated sodium chloride solution until neutral. The organic phase is then dried over sodium sulfate and evaporated in a rotary evaporator. N-Methyl-3-(2,3-dimethyl-6-benzofuranyl)-glutarimide thus obtained as sand-coloured crystals of melting point 182°-185° crystallises spontaneously.

Workup

  1. temperaturethe reaction mixture is heated to the boiling point for 61/2 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ether
  4. washthe organic phase is washed with sodium bicarbonate and saturated sodium chloride solution until neutral
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-2441cdb3ad53447fa2bda12a01a2d47e
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

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