Pyridine → HCID 19594543, compound

HRID 612379Notes

Reaction equation

HRID 612379 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[N:25]1C=CC=CC=1>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][C:3]2[C:4]([NH2:25])=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=2[S:21]([CH3:20])(=[O:23])=[O:22])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19594503HCID 19594503, compound

Product 1

HCID 19594543HCID 19594543, compound

Procedure

4-Amino-3-(4-chlorophenylthio)-benzenesulphonamide (0.43 g; 1.37 mmol) was dissolved in pyridine (10 ml) and at 0° C. methanesulphonic acid chloride (4.7 g; 41.0 mmol) was added dropwise. The solution came up to ambient temperature overnight, was then poured onto water and extracted with CH2Cl2. The solvent was evaporated off and the residue was stirred in dioxan (10 ml)/2N aqueous NaOH (10 ml). After acidifying with 2N HC1, the mixture was extracted with ethyl acetate, dried over MgSO4 and evaporated down. The residue was recrystallised from CH2Cl2. Yield: 0.28 g=52% 13C (100 MHz, DMSO-d6) δ 141.50, 140.23, 133.03, 132.82, 132.73, 129.79, 129.78, 129.46, 126.16, 123.90, 41.03

Workup

  1. additionwas added dropwise
  2. additionwas then poured onto water
  3. extractionextracted with CH2Cl2
  4. customThe solvent was evaporated off
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. customevaporated down
  8. customThe residue was recrystallised from CH2Cl2

Sources & evidence

ORD record
ord-92d50991baba4fa7a1491aba57c257bc
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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