Triethylamine → HCID 59653666, compound

HRID 2052757Notes

Reaction equation

HRID 2052757 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].Cl[CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(Cl)Cl>[CH:16]([S:17]([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:19])=[O:18])=[CH2:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59653666HCID 59653666, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5.38 g (30.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide and CH2Cl2 (120 ml) is successively treated with 2-chloroethanesulfonyl chloride (6.3 ml, 60.0 mmol) at room temperature and triethylamine (12.5 ml, 90.0 mmol) at 0° C. Stirring is continued for 1.5 h at room temperature and the resulting reaction mixture is treated with 10% aqueous sodium carbonate solution (100 ml) and ethyl acetate (200 ml). The organic phase is washed with. water (100 ml), dried over Na2SO4, and concentrated. The residue is further dried under vacuum, providing 5.89 g of pure product as light-yellow solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.53 (d, 1H), 1.76-1.81 (m, 1H), 3.12 (s, 2H), 3.48 (s, 2H), 6.17 (s, 2H), 6.29 (d, 1H), 6.53 (d, 1H), 6.78 (dd, 1H).

Workup

  1. customat 0° C
  2. customthe resulting reaction mixture
  3. washThe organic phase is washed with
  4. dry with materialwater (100 ml), dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is further dried under vacuum

Sources & evidence

ORD record
ord-a0d88ed64dbd462b888867a09f04ed12
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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