Acetic Anhydride → HCID 18385718, compound

HRID 2298336Notes

Reaction equation

HRID 2298336 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:7][C:6]=1[Cl:25])(=[O:4])=[O:3].[C:26](OC(=O)C)(=[O:28])[CH3:27].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[C:26]([NH:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13](=[O:18])[C:12]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:7][C:6]=1[Cl:25])(=[O:3])=[O:4])(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18385874HCID 18385874, compound

Product 1

HCID 18385718HCID 18385718, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

150 mg of 5-{4-(aminosulfonyl)-3-chlorophenyl}-2,2-dimethyl-4-phenyl-3(2furanone (Example 367) in 10 ml dichloromethane was reacted with 0.3 ml acetic anhydride in the presence of 0.5 ml triethylamine and 15 mg of 4-(N,N-dimethylamino)pyridine at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, which was followed by extraction with 30 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and then was purified by column chromatography (hexane/ethylacetate 2:1) to afford 113 mg of 5-[4-{(acetylamino)sulfonyl}-3-chlorophenyl]-2,2-dimethyl-4-phenyl-3(2H)-furanone as a solid. mp: 194-195° C. NMR: δ1.57 (s, 6H), 2.10 (s, 3H), 7.27 (m, 2H), 7.40 (m, 3H), 7.68 (dd, J=8.4, 1.8 Hz, 1H), 7.85 (d, J=1.5 Hz, 1H), 8.18 (d, J=8.1 Hz, 1H), 8.45 (br s, 1H). IR (cm−1): 3195, 3104, 1698, 1377, 1164.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, which
  2. extractionwas followed by extraction with 30 ml water and dichloromethane (30 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/ethylacetate 2:1)

Sources & evidence

ORD record
ord-2c51db4b001a4c4d8eb403f1daab98d7
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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