p-Chlorothiophenol → HCID 19594473, compound

HRID 612377Notes

Reaction equation

HRID 612377 reaction equation
Cl[C:2]1[CH:3]=[C:4]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(Cl)Cl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:2]2[CH:3]=[C:4]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 19594524HCID 19594524, compound

Product 1

HCID 19594473HCID 19594473, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Chloro-4-nitrobenzenesulphonamide (1.08 g; 4.53 mmol), 4-chlorothiophenol (0.66 g; 4.53 mmol) and K2CO3 (0.64 g; 4.60 mmol) were refluxed in dioxan (30 ml) for 3 hours. The mixture was then diluted with CH2Cl2, filtered and washed with water. The organic phase was dried over MgSO4 and evaporated down. The product was recrystallised from petroleum ether/ethyl acetate. Yield: 1.0 g=64% 13C (100 MHz, DMSO-d6) δ 148.57, 146.43, 138.07, 137.08, 135.76, 130.70, 128.74, 127.27, 125.43, 123.52

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated down
  5. customThe product was recrystallised from petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-4006b000cd904d208df597f54eeab82d
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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