4-Toluenesulfonyl chloride → N,N-bis(2-chloroethyl)-p-toluenesulphonamide

HRID 421522

반응식

HRID 421522 반응식
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].CCN(CC)CC.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][Cl:8])[S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

생성물 1

HCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamide수율 80.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of bis(2-chloroethyl)amine hydrochloride (4.68 g, 26.2 mmol) in dry THF (50 mL) was added Et3N (18.3 mL, 131 mmol) at 0° C. and the mixture was stirred for 15 min. p-Toluenesulfonyl chloride (5.00 g, 26.25 mmol) and DMAP (a spatula pinch) were added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. When TLC analysis showed complete conversion, the mixture was filtered to remove the Et3N.HCl and extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography to afford N,N-bis(2′-chloroethyl)-4-methylbenzenesulfonamide (6.22 g, 80% yield).

후처리

  1. additionwere added
  2. filtrationthe mixture was filtered
  3. customto remove the Et3N.HCl
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-6c4eed1389624149a76331714ac9fde2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101238B2

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