Chloromethyl Methyl Ether → HCID 59428123, compound

HRID 75983Notes

Reaction equation

HRID 75983 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11].C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][CH2:31]Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:29][O:30][CH3:31])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 59428157HCID 59428157, compound

Product 1

HCID 59428123HCID 59428123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-bromo-4-chloro-phenyl)-4-tert-butyl-benzenesulfonamide (1.00 g, 2.49 mmol) and K2CO3 (1.72 g, 12.4 mmol) in 8 mL anhydrous THF was added chloromethyl methyl ether (299 mg, 3.73 mmol). The resultant heterogeneous solution was stirred for 60 minutes at ambient temperature and the solids were subsequently removed via filtration. The filtrate was subsequently concentrated in vacuo and the residue was dissolved in EtOAc. The organics were washed with saturated Na2CO3, dried over MgSO4, and evaporated in vacuo. The resultant residue was then purified via automated silica gel chromatography to afford the desired protected sulfonamide: MS (ES) M+H expected 446.0, found 446.0.

Workup

  1. customthe solids were subsequently removed via filtration
  2. concentrationThe filtrate was subsequently concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organics were washed with saturated Na2CO3
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe resultant residue was then purified
  8. customto afford the

Sources & evidence

ORD record
ord-8086d8d4360a485584a433cf86aa7b3a
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

Loading…