Potassium Carbonate → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

HRID 472378

反応式

HRID 472378 の反応式
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1>CC(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 68528p-Bromobenzyl chlorideHCID 6484228Thiomorpholine 1,1-dioxide

生成物 1

HCID 523254684-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a well stirred suspension of thiomorpholine 1,1-dioxide (0.36 g, 2.7 mmol) and potassium carbonate (0.37 g, 2.7 mmol) in acetone (5 mL) was added 1-bromo-4-chloromethyl-benzene (0.50 g, 2.4 mmol). The mixture was stirred for 48 hours at room temperature. The mixture was filtered and the volatiles were evaporated. The residue was suspended in ether (100 mL), filtered and evaporated to a solid. The material was purified via chromatography utilizing an ISCO automated purification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane). 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide was isolated as a white solid (0.72 g, 97%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.47 (d, J=7.6 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 3.60 (s, 2H), 3.08-2.94 (m, 8H). MS=304, 306 (MH)+.

後処理

  1. stirringThe mixture was stirred for 48 hours at room temperature
  2. filtrationThe mixture was filtered
  3. customthe volatiles were evaporated
  4. filtrationfiltered
  5. customevaporated to a solid
  6. customThe material was purified via chromatography
  7. custompurification apparatus (24 g silica gel column 10%→100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-d31aa3f94bd74546ac9e0316d120c040
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

関連ノート

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