Hydrochloric Acid → N-(5-chloro-thiazol-2-yl)-3-cyano-4-fluorobenzenesulfonamide

HRID 1401952Notes

Reaction equation

HRID 1401952 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.N1C=CC=CC=1.[C:15]([C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[F:23])#[N:16].Cl>ClCCl>[Cl:8][C:5]1[S:4][C:3]([NH:2][S:24]([C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([C:15]#[N:16])[CH:18]=2)(=[O:25])=[O:26])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Product 1

HCID 59436522N-(5-chloro-thiazol-2-yl)-3-cyano-4-fluorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 2-amino-5-chlorothiazole-hydrochloride (3.76 g, 22.0 mmol) in dichloromethane (20 ml) was added pyridine (8.09 ml, 100 mmol). 3-cyano-4-fluorobenzenesulfonyl chloride (4.39 g, 20 mmol) dissolved in dichloromethane (5 mL) and was added to the reaction mixture dropwise at room temperature. After stirring for 48 hours at room temperature, 1 N HCl (100 mL) was poured into the reaction and the mixture was extracted with dichloromethane/methanol (v/v=95/5, 100 ml) three times. The collected organic layer was evaporated in vacuo and dried over MgSO4 to obtain the crude residue. The crude residue was washed with dichloromethane (10 mL) and filtered to afford pale yellow solid as the title compound. LCMS Rt=1.39 minutes MS m/z 318 [M35ClH]+, 320 [M37ClH]+ 1HNMR (d6-DMSO): δ 7.59 (s, 1H), 7.66-7.73 (m, 1H), 8.15-8.21 (m, 1H), 8.33-8.37 (m, 1H).

Workup

  1. additionwas added to the reaction mixture dropwise at room temperature
  2. extractionthe mixture was extracted with dichloromethane/methanol (v/v=95/5, 100 ml) three times
  3. customThe collected organic layer was evaporated in vacuo
  4. dry with materialdried over MgSO4
  5. customto obtain the crude residue
  6. washThe crude residue was washed with dichloromethane (10 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-92f89ad417a64a30bc5ae6e263c7e091
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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