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

HRID 472378

반응식

HRID 472378 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-d31aa3f94bd74546ac9e0316d120c040
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

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