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

HRID 421522

反応式

HRID 421522 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c4eed1389624149a76331714ac9fde2
出典データセット
uspto-grants-2012_01
特許番号
US08101238B2

関連ノート

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