Water → HCID 23333523, compound

HRID 904088Notes

Reaction equation

HRID 904088 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:26])([F:25])[C:8]([C:14]1[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([NH2:24])=[CH:16][CH:15]=1)([OH:13])[C:9]([F:12])([F:11])[F:10].O>N1C=CC=CC=1>[F:6][C:7]([F:25])([F:26])[C:8]([C:14]1[CH:15]=[CH:16][C:17]([NH:24][S:2]([CH3:1])(=[O:4])=[O:3])=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH:23]=1)([OH:13])[C:9]([F:10])([F:12])[F:11]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 54197899HCID 54197899, compound

Product 1

HCID 23333523HCID 23333523, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 2.50 g (22 mmole) of methanesulfonyl chloride dropwise to 4.57 g (15 mmole) of methyl 5-(hexafluoro-2-hydroxy-2-propyl)anthranilate in 25 ml of pyridine and allow to stand overnight. Pour the reaction into H2O and extract with Et2O. Wash the Et2O with 1N HCl and extract with 1N NaOH. Acidify the NaOH and extract with Et2O. Dry, concentrate and recrystallize from Et2O-hexane to obtain 4'-(hexafluoro-2-hydroxy-2-propyl)-2'-(methoxycarbonyl)methanesulfonanilide; m.p. 147°-148° C.

Workup

  1. additionPour
  2. extractionextract with Et2O
  3. washWash the Et2O with 1N HCl
  4. extractionextract with 1N NaOH
  5. extractionextract with Et2O
  6. customDry
  7. concentrationconcentrate
  8. customrecrystallize from Et2O-hexane

Sources & evidence

ORD record
ord-ed96c9d34fba4ae3be75ef62096dcdee
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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