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

HRID 356519노트

반응식

HRID 356519 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f2fbecccf894fc4bf9f63a38edd3f11
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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