Methanol → Sulindac

HRID 890830Notes

Reaction equation

HRID 890830 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22]([OH:24])=[O:23].C[OH:26]>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:19])=[O:26])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22]([OH:24])=[O:23]

Participants

3

Reactant 2

HCID 887MethanolHCID 5352624Sulindac Sulfide

Product 1

HCID 1548887SulindacYield 87%

Conditions

Temperature
5 °C

Procedure

(Z)-5-fluoro-2-methyl-1-[[4-(methylthio)-phenyl]methylene]-1H-indene-3-acetic acid (5 g, 14.7 mmoles) is dissolved in methanol (40 ml). The solution is added with 5.4 g (14.26 mmoles) of 73% w/w ε-phthalimidoperhexanoic acid, keeping the temperature at about 20° C. After 18 h, the solution is concentrated to 15 ml and cooled to 5° C. The precipitate is filtered and dried. 4.6 g of (Z)-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)-phenyl]methylene]-1H-indene-3-acetic acid (sulindac) is obtained.

Workup

  1. additionThe solution is added with 5.4 g (14.26 mmoles) of 73% w/w ε-phthalimidoperhexanoic acid
  2. customat about 20° C
  3. concentrationthe solution is concentrated to 15 ml
  4. filtrationThe precipitate is filtered
  5. customdried

Sources & evidence

ORD record
ord-e424d69b24d84332b7f34289641ceabb
Source dataset
uspto-grants-2006_02
Patent number
US06998490B2

Reaction notes

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