Triethylamine → HCID 12274051, compound

HRID 1733682Notes

Reaction equation

HRID 1733682 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(N(CC)CC)C.O1CCOCC1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1C=CC=CC=1>[CH3:22][S:23]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 31297Methanesulfonyl chlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 12274051HCID 12274051, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

N-Hydroxysuccinimide (11.5 g) and triethylamine (14.0 ml) are suspended into a mixture of benzene (100 ml) and dioxane (50 ml), and thereto is added dropwise a solution of methanesulfonyl chloride (7.8 ml) in benzene (20 ml) with stirring under ice-cooling and the mixture is stirred for 1 hour. After allowing to stand overnight, the solvent is distilled off. To the residue is added water and the resulting crystals are separated by filtration, washed with water and dried to give N-methanesulfonyloxysuccinimide (6.3 g), melting point: 148°-150° C. The product is recrystallized from ethyl acetate-petroleum ether to give crystals having a melting point of 150°-152° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 1 hour
  3. distillationthe solvent is distilled off
  4. additionTo the residue is added water
  5. customthe resulting crystals are separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-fda6cd9744e244f8ad13ffcf37abe724
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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