Hydrochloric Acid → Toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(4-cyano-benzenesulfonylamino)-5-methyl-phenyl] ester

HRID 356519Notes

Reaction equation

HRID 356519 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)#[N:25].N1C=CC=CC=1.Cl>C(Cl)Cl>[C:20]([C:4]1[CH:3]=[C:2]([NH:1][S:32]([C:29]2[CH:28]=[CH:27][C:26]([C:24]#[N:25])=[CH:31][CH:30]=2)(=[O:34])=[O:33])[C:7]([CH3:8])=[CH:6][C:5]=1[S:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 10569823Toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester

Product 1

HCID 10673378Toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(4-cyano-benzenesulfonylamino)-5-methyl-phenyl] ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester obtained from Example HHHH (0.20 g, 0.57 mmol), 4-cyanobenzenesulfonyl chloride (0.15 g, 0.74 mmol), pyridine (7 mL) and CH2Cl2 (1 mL) was stirred at room temperature under nitrogen overnight. 1N HCl was then added and the mixture was extracted with EtOAc. The organic phase was washed with 1N HCl and brine, dried (Na2SO4), filtered and concentrated. The resulting residue was flash chromatographed on silica gel, eluting with 19:1 CHCl3 :EtOAc to afford the title compound. 1H NMR (CDCl3) δ 1.16 (s, 9 H), 1.98 (s, 3 H), 2.43 (s, 3 H), 6.49 (s, 1 H), 7.23 (s, 1 H), 7.27 (d, partially obscured by CDCl3, 2 H), 7.48 (d, 2 H), 7.78 (d, 2 H), 7.87 (d, 2 H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with 1N HCl and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel
  7. washeluting with 19:1 CHCl3

Sources & evidence

ORD record
ord-1f2fbecccf894fc4bf9f63a38edd3f11
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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