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Triethylamine → toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester

HRID 1003866
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HRID 1003866 반응식
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[C:19]([C:23]1[C:24]([SH:37])=[CH:25][C:26]([CH3:36])=[C:27]([O:29][S:30](=[O:35])(=[O:34])[N:31]([CH3:33])[CH3:32])[CH:28]=1)([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl>[C:19]([C:23]1[CH:28]=[C:27]([O:29][S:30](=[O:34])(=[O:35])[N:31]([CH3:32])[CH3:33])[C:26]([CH3:36])=[CH:25][C:24]=1[S:37][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 10662229Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

생성물 1

HCID 10695175toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

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온도
0 °C

실험 절차

To a round bottom flask equipped with a magnetic stirrer and addition funnel were added tosyl bromide (1.64 g, 7.0 mmol), CCl4 (25 mL), and NEt3 (0.98 mL, 7.0 mmol). The ensuing slurry was then cooled to 0° C. A solution of 1.07 g (3.5 mmol) of dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester (prepared in Example TTT) in CCl4 (25 mL) was added dropwise to the slurry. Addition was complete in 1.0 hour. After addition was complete, the ice bath was removed and the reaction was stirred at room temperature overnight. The mixture was diluted with CH2Cl2, washed with brine, dried (MgSO4), and concentrated. The residue was taken up in a small amount of EtOAc and triturated with hexane. The product was filtered and dried under high vacuum to yield the title compound. 1H NMR (CDCl3) δ 1.15 (s, 9 H), 2.23 (s, 3 H), 2.37 (s, 3 H), 3.02 (s, 6 H), 7.19 (d, 2 H), 7.22 (s, 1 H), 7.33 (s, 1 H), 7.40 (d, 2 H).

후처리

  1. customTo a round bottom flask equipped with a magnetic stirrer and addition funnel
  2. additionAddition
  3. additionAfter addition
  4. customthe ice bath was removed
  5. additionThe mixture was diluted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customtriturated with hexane
  10. filtrationThe product was filtered
  11. customdried under high vacuum

출처 및 근거

ORD 기록
ord-57abfc2ce99f44349305ab8118f98ffd
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06046355

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