Methylamine → (S)-N-Methylhydroxysuccinimide

HRID 4793

Reaction equation

HRID 4793 reaction equation
[C:1]([OH:9])(=O)[C@H:2]([CH2:4][C:5](O)=[O:6])[OH:3].[CH3:10][NH2:11]>C1(C)C=CC=CC=1>[OH:3][C@H:2]1[CH2:4][C:5](=[O:6])[N:11]([CH3:10])[C:1]1=[O:9]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 222656L-Malic Acid

Product 1

HCID 13726417(S)-N-Methylhydroxysuccinimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 134 g (1 mole) of (S)-malic acid in 700 ml of toluene was added 97 ml of 40% aqueous methylamine. The temperature slowly rose to 50° C. After 0.5 hr the stirred mixture was heated to reflux and the water was collected in a Dean-Stark trap for 48 hours. A total of 93 ml of water was collected. The toluene residue was treated with 300 ml of ethanol and concentrated on the rotary evaportor. The residue was distilled. The yield of product obtained was 101 g (78%), b.p. 140°/2 mm; 145°/0.5 mm.

Workup

  1. customslowly rose to 50° C
  2. temperatureAfter 0.5 hr the stirred mixture was heated
  3. temperatureto reflux
  4. customthe water was collected in a Dean-Stark trap for 48 hours
  5. customA total of 93 ml of water was collected
  6. additionThe toluene residue was treated with 300 ml of ethanol
  7. concentrationconcentrated on the rotary evaportor
  8. distillationThe residue was distilled
  9. customThe yield of product obtained
  10. custom145°/0.5 mm

Sources & evidence

ORD record
ord-b804369893e54bd59770ee9a23839cc6
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

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