Triethylamine → N-Carbomethoxy-N-cyclohexylsulfamyl-O-methylisourea

HRID 246837

반응식

HRID 246837 반응식
C(N(CC)CC)C.[C:8]([NH:12][C:13](=[NH:16])[O:14][CH3:15])([O:10][CH3:11])=[O:9].[CH:17]1([NH:23][S:24](Cl)(=[O:26])=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C1COCC1.C(Cl)Cl>[C:8]([N:12]([S:24](=[O:26])(=[O:25])[NH:23][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13](=[NH:16])[O:14][CH3:15])([O:10][CH3:11])=[O:9]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 12914615Cyclohexylsulfamyl chlorideHCID 137319931Methyl N-(iminomethoxymethyl)carbamate

생성물 1

HCID 21269103N-Carbomethoxy-N-cyclohexylsulfamyl-O-methylisourea

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

Triethylamine (112 g) is added to a stirred solution of N-carbomethoxy-O-methylisourea (132.1 g) in anhydrous THF (900 ml). The solution is cooled to -70° C. under an N2 atmosphere and solution of cyclohexylsulfamoyl chloride (198 g) in anhydrous THF (400 ml) is added dropwise to the reaction mixture. The reaction mixture is warmed to RT filtered through Celite®, washed with anhydrous THF and evaporated to yield an oil which is taken up in methylene chloride, washed with 0.5N HCl and allowed to stand overnight. The organic layer is washed with 0.5N HCl, dried, filtered, washed with methylene chloride, evaporated and dried under high vacuum affording the desired product as an oil which is used in the next step without further purification.

후처리

  1. temperatureThe reaction mixture is warmed to RT
  2. filtrationfiltered through Celite®
  3. washwashed with anhydrous THF
  4. customevaporated
  5. customto yield an oil which
  6. washwashed with 0.5N HCl
  7. washThe organic layer is washed with 0.5N HCl
  8. customdried
  9. filtrationfiltered
  10. washwashed with methylene chloride
  11. customevaporated
  12. customdried under high vacuum

출처 및 근거

ORD 기록
ord-255c3752580c4567bd3b121ac161a56e
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04704388

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