Sulfuric Acid → 6-Bromo-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

HRID 467556ノート

反応式

HRID 467556 の反応式
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:10]=[CH:11][CH:12]=1.[CH3:26]OCOC.C(Cl)Cl>C1(C)C=CC=CC=1.CCOCC>[Br:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:11][CH:12]=1)[CH2:26][N:15]([S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH2:14][CH2:13]2

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 8020DimethoxymethaneHCID 21975863N-(3-Bromophenethyl)-4-methylbenzenesulfonamide

生成物 1

HCID 219758586-Bromo-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline収率 90%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a stirred solution of sulfuric acid (60% w/w, 20 g) in 32 mL of toluene at r.t. was added 7.60 g of N-[2-(3-bromo-phenyl)-ethyl]-4-methyl-benzenesulfonamide, followed by 32 mL of dimethoxymethane. The reaction mixture was heated over an oil bath set at 50° C. externally with stirring under nitrogen for 15 h. LC/MS: retention time=4.549 min, MS 366/368. TLC (DCM): SM Rf=0.35, product Rf=0.65. The reaction was complete as judged by TLC. The reaction mixture was cooled to r. t. and diluted with ether (100 mL). The two layers were separated and the aqueous layer was extracted with ether (25 mL). The combined ethereal solution was washed with water (25 mL), saturated sodium bicarbonate (25 mL) and brine (20 mL), sequentially. Then, the ethereal solution was dried over anhydrous granular potassium carbonate, filtered, and concentrated in vacuo. The crude product, a solid after standing, was re-crystallized from ether (75 mL) and pentane (100 mL). The material was collected by suction filtration and dried under vacuum to obtain 6.6 g (90%) of the title compound as a white crystalline solid:

後処理

  1. temperatureThe reaction mixture was heated over an oil bath
  2. customset at 50° C.
  3. temperatureThe reaction mixture was cooled
  4. customThe two layers were separated
  5. extractionthe aqueous layer was extracted with ether (25 mL)
  6. washThe combined ethereal solution was washed with water (25 mL), saturated sodium bicarbonate (25 mL) and brine (20 mL)
  7. dry with materialThen, the ethereal solution was dried over anhydrous granular potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customwas re-crystallized from ether (75 mL) and pentane (100 mL)
  11. filtrationThe material was collected by suction filtration
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-ee1c922deae14883bb21393a77150b85
出典データセット
uspto-grants-2014_01
特許番号
US08623877B2

反応ノート

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