Hydrochloric Acid → HCID 59653663, compound

HRID 2052759Notes

Reaction equation

HRID 2052759 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[CH:10]2[CH:5]([CH:6]3[CH2:13][CH:9]2[CH:8]=[CH:7]3)[C:3]1=[O:4].N1C=CC=CC=1.[Cl:20][CH2:21][CH2:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:20][CH2:21][CH2:22][S:23]([O:1][N:2]1[C:11](=[O:12])[CH:10]2[CH:5]([CH:6]3[CH2:13][CH:9]2[CH:8]=[CH:7]3)[C:3]1=[O:4])(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59653663HCID 59653663, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 12.5 g (70.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide and pyridine (6.2 ml, 77.0 mmol) in CH2Cl2 (105 ml) is treated dropwise with 2-chloroethanesulfonyl chloride (7.36 ml, 70.0 mmol) at 0° C., according to the procedure of W. C. Groutas, M. A. Stanga, J. C. Castrisos, E. J. Schatz, M. J. Brubaker J. Pharm. Sci. 1990, 79, 886-88. After stirring overnight at room temperature, the reaction mixture is diluted with ethyl acetate (280 ml) and then treated with 5% aqueous HCl (130 ml). The layers are separated and the aqueous layer is extracted once with ethyl acetate (280 ml). The combined organic extracts are dried over Na2SO4 and evaporated under reduced pressure, leaving a colorless oil which solidifies when further dried under vacuum. 15.6 g (73%) of the product are obtained as a white solid.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted once with ethyl acetate (280 ml)
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. customevaporated under reduced pressure
  5. customleaving a colorless oil which
  6. customfurther dried under vacuum

Sources & evidence

ORD record
ord-af4a6c60321c4c4da44196852641e6f4
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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