Water → Tetrahydrophthalimide

HRID 727750Notes

Reaction equation

HRID 727750 reaction equation
[NH2:1]C1C=CC=CC=1.[C:8]12[C:17](=[O:18])O[C:14](=[O:15])[C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13]2.O>C(O)(=O)C>[C:17]1(=[O:18])[NH:1][C:14](=[O:15])[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:8]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 124753,4,5,6-Tetrahydrophthalic anhydride

Product 1

HCID 34024Tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.5 g (0.017 mole) of the above aniline and 2.7 g (0.018 mole) of cyclohexene-1,2-dicarboxylic anhydride in 70 ml of glacial acetic acid are stirred for 3 hours at 70° C. After the mixture has been cooled, 100 ml of water are added and the precipitate is filtered off, washed with water and dried. 3.5 g (52%) of N-[4-tetrahydropyran-4-ylmethyl)-3,3-dihydro-2H-1,4-benzoxazin -3-on-6-yl]-3,4,5,6-tetrahydrophthalimide (mp. 187-189° C.) are obtained.

Workup

  1. temperatureAfter the mixture has been cooled
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c0346460ea7d42bcb891d3ae1b5a0c53
Source dataset
uspto-grants-1991_09
Patent number
US05045105

Reaction notes

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