Acetic Anhydride → methyl 1-[4-(N-acetylaminosulfonyl)phenyl]methylene-5-methoxy-2-methyl-1H-3-indenylacetate

HRID 542228Notes

Reaction equation

HRID 542228 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:13]2[CH3:28])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([NH:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:13]2[CH3:28])=[CH:9][CH:10]=1)(=[O:3])=[O:4])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70401818methyl 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate

Product 1

HCID 67583860methyl 1-[4-(N-acetylaminosulfonyl)phenyl]methylene-5-methoxy-2-methyl-1H-3-indenylacetateYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4a (100 mg) in pyridine (5 ml) was added acetic anhydride (2 ml). The mixture was heated at 110° for 1 hour and concentrated in vacuo. The crude mixture was purified via preparative tlc using 2000 μm silica gel plates developed with 30% ethyl acetate in chloroform. The isolated product was recrystallized from acetone-hexane to give pure Z methyl 1-[4-(N-acetylaminosulfonyl)phenyl]methylene-5-methoxy-2-methyl-1H-3-indenylacetate (55 mg, 50%): m.p. 172.5°-174.5° C.

Workup

  1. temperatureThe mixture was heated at 110° for 1 hour
  2. concentrationconcentrated in vacuo
  3. customThe crude mixture was purified via preparative tlc
  4. customThe isolated product was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-590f05cf26ed4032b1bc7240d1d17c43
Source dataset
uspto-grants-1987_04
Patent number
US04656190

Reaction notes

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