Sodium Chloride → N-[4-(4,5-Dihydrothiazol-2-yl)benzyl]-4-fluorobenzenesulfonamide

HRID 2359821Notes

Reaction equation

HRID 2359821 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].N[CH2:22][CH2:23][SH:24].[Cl-].[Na+]>C(O)C>[S:24]1[CH2:23][CH2:22][N:2]=[C:1]1[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6058CysteamineHCID 47298773N-(4-Cyanobenzyl)-4-fluorobenzenesulfonamide

Product 1

HCID 66717716N-[4-(4,5-Dihydrothiazol-2-yl)benzyl]-4-fluorobenzenesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(4-cyanobenzyl)-4-fluorobenzenesulfonamide (1.23 g, 4.24 mmol) obtained in Reference Example 7-(a) in ethanol (5 ml) was added 2-aminoethanethiol (0.426 g, 5.52 mmol), which was deaerated under reduced pressure, followed by argon substitution. This reaction mixture was then heated to reflux for 6 hours. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; chloroform:ethyl acetate=7:3 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.32 g) as a white solid. (Yield: 89%)

Workup

  1. temperatureThis reaction mixture was then heated
  2. temperatureto reflux for 6 hours
  3. customAfter completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9df293bfaa4442a9adace67c16e3efa
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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