Water → HCID 23333501, compound

HRID 904089Notes

Reaction equation

HRID 904089 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:13]=[C:12]([C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])[CH:11]=[C:10]([O:24][CH3:25])[C:8]=1[NH2:9].O>N1C=CC=CC=1>[Br:6][C:7]1[CH:13]=[C:12]([C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:16])[F:17])[CH:11]=[C:10]([O:24][CH3:25])[C:8]=1[NH:9][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 54060608HCID 54060608, compound

Product 1

HCID 23333501HCID 23333501, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 2.5 g (22 mmole) of methanesulfonyl chloride dropwise to 5.5 g (15 mmole) of 2-bromo-4-(hexafluoro-2-hydroxy-2-propyl)-6-methoxyaniline in 30 ml of pyridine below 10° C. Allow to stand overnight. Pour into H2O and decant. Dissolve the oil in Et2O, wash with 1N HCl and extract with 1N NaOH. Acidify the NaOH with HCl and extract with Et2O. Dry and concentrate. Chromatograph the oil on silica gel, eluting with CHCl3. Recrystallize from CH2Cl2 to obtain 2'-bromo-4'-(hexafluoro-2-hydroxy-2-propyl)-6'-methoxymethanesulfonanilide; m.p. 38°-41° C.

Workup

  1. customdecant
  2. dissolutionDissolve the oil in Et2O
  3. washwash with 1N HCl
  4. extractionextract with 1N NaOH
  5. extractionextract with Et2O
  6. customDry
  7. concentrationconcentrate
  8. washChromatograph the oil on silica gel, eluting with CHCl3
  9. customRecrystallize from CH2Cl2

Sources & evidence

ORD record
ord-110c2b9fcc054e59bc17e80c20dc3c40
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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