Diethyl Ether → 3-(Chloroacetamido)-2-hydroxyphenyl sulfonamide

HRID 1651478Notes

Reaction equation

HRID 1651478 reaction equation
C([C:5]1[CH:6]=[C:7]([NH:21][C:22](=[O:25])[CH2:23][Cl:24])[C:8]([O:19]C)=[C:9]([S:11]([NH:14]C(C)(C)C)(=[O:13])=[O:12])[CH:10]=1)(C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=C(C)C=1.C(OCC)C>O>[Cl:24][CH2:23][C:22]([NH:21][C:7]1[C:8]([OH:19])=[C:9]([S:11]([NH2:14])(=[O:12])=[O:13])[CH:10]=[CH:5][CH:6]=1)=[O:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7929M-XyleneHCID 6451240Aluminum(III) ChlorideHCID 150295875-t-butyl-2-methoxy-3-(chloroacetamido) phenyl N-t-butylsulfonamide

Product 1

HCID 150295883-(Chloroacetamido)-2-hydroxyphenyl sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-t-butyl-2-methoxy-3-(chloroacetamido) phenyl-N-t-butyl-sulfonamide (8.0 g), aluminium chloride (16.4 g) and m-xylene (80 ml) was heated at 95° C. with stirring for 16 hours under nitrogen. The mixture was then poured into a beaker containing diethyl ether (300 ml) and water (300 ml) and stirred at ambient temperature for 15 minutes. The organic layer is separated and dried over sodium sulphate and concentrated under vacuum in order to remove all diethyl ether. The residual solution was cooled and hexane added to precipitate the title compound (4.7 g).

Workup

  1. additionThe mixture was then poured into a beaker
  2. stirringstirred at ambient temperature for 15 minutes
  3. customThe organic layer is separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum in order
  6. customto remove all diethyl ether
  7. temperatureThe residual solution was cooled
  8. additionhexane added
  9. customto precipitate the title compound (4.7 g)

Sources & evidence

ORD record
ord-1279d3f0b3a14fc394a6f06d92ccfada
Source dataset
uspto-grants-1990_05
Patent number
US04929269

Reaction notes

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