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

HRID 1003866
ノート
印刷プレビュー

反応式

HRID 1003866 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-57abfc2ce99f44349305ab8118f98ffd
出典データセット
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06046355

反応ノート

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