Benzenesulfonyl chloride → (3-Aminocyclohexyl)(phenylsulfonyl)amine

HRID 352172

반응식

HRID 352172 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH2:8])[CH2:3]1.[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)Cl>[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH2:3]1

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 188141,3-Cyclohexanediamine

생성물 1

HCID 22714123(3-Aminocyclohexyl)(phenylsulfonyl)amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of 1,3-diaminocyclohexane (1.14 g, 10 mmol, undetermined isomer mixture) in methylene chloride (50 mL) was cooled to 0° C. and phenylsulfonyl chloride (0.64 mL, 5 mmol) was added dropwise. The mixture was stirred at 0° C. for 4 h, then 1N sodium hydroxide solution (10 mL) was added and the mixture stirred an additional 5 min. The phases were separated, the organic phase was dried (K2CO3), filtered, and concentrated in vacuo. Toluene was added and the mixture re-concentrated to remove any remaining diamine, to give 0.77 g of a semi solid. 1H—NMR was consistent with the desired structure. MS (ion spray) 255 (M+1).

후처리

  1. stirringthe mixture stirred an additional 5 min
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionToluene was added
  7. concentrationthe mixture re-concentrated
  8. customto remove any remaining diamine
  9. customto give 0.77 g of a semi solid

출처 및 근거

ORD 기록
ord-00c7fddcef0447a38fcc09444aa75ea4
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743794B2

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