Sulfuryl chloride → tert-butyl N-[3-(chlorosulfonyl)phenyl]-N-methylcarbamate

HRID 29190

반응식

HRID 29190 반응식
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:6].C([Li])CCC.[S:22](Cl)([Cl:25])(=[O:24])=[O:23]>C1COCC1>[C:10]([O:9][C:7]([N:5]([CH3:6])[C:4]1[CH:14]=[CH:15][CH:16]=[C:2]([S:22]([Cl:25])(=[O:24])=[O:23])[CH:3]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 24648Sulfuryl chlorideHCID 22997148N-BOC-N-Methyl-3-bromoanilineHCID 178418339Butyllithium

생성물 1

HCID 22996452tert-butyl N-[3-(chlorosulfonyl)phenyl]-N-methylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

3-Bromo-N-tert-butoxycarbonyl-N-methylaniline (0.358 g, 1.2 mmol) was dissolved in freshly distilled THF (5 ml) under a N2 atmosphere. The solution was chilled to −78° C. and n-butyl lithium (0.750 ml, 2.0 M solution in cyclohexane, 1.5 mmol) was added. After 15 minutes, sulfuryl chloride (0.121 ml, 1.5 mmol) was added and the reaction was allowed to warm to room temperature and stirring was continued overnight. THF was removed by evaporation and the resulting residue was diluted in EtOAc. Organic phase was washed with H2O and brine before being dried with MgSO4. The solvent was removed in vacuo. Purification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9 and then to 1:4). Recovered 0.089 g (23%) of the product as a colorless oil. Rf=0.14 (1:9 EtOAc/Hex). 1H NMR (CDCl3) 7.96 (1H,s), 7.80 (1H,d), 7.68 (1H,d), 7.57 (1H,t), 3.33 (3H,s), 1.50 (9H,s).

후처리

  1. temperatureto warm to room temperature
  2. waitwas continued overnight
  3. customTHF was removed by evaporation
  4. additionthe resulting residue was diluted in EtOAc
  5. washOrganic phase was washed with H2O and brine
  6. dry with materialbefore being dried with MgSO4
  7. customThe solvent was removed in vacuo
  8. customPurification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9
  9. customRecovered 0.089 g (23%) of the product as a colorless oil

출처 및 근거

ORD 기록
ord-950b4dc6d8054b6cb3d25456521aec7b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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