Water → 5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

HRID 1845149노트

반응식

HRID 1845149 반응식
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866521075-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

생성물 1

HCID 657697715-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A round bottom flask was charged with 5-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide (1.40 g, 4.87 mmol), THF (40 mL), triphenylphosphine (1.6 g, 6.43 mmol) and water (0.11 mL, 6.43 mmol) at 0° C. and the reaction was stirred at room temperature over night. The solvents were removed and the residue was dissolved in MTBE and 20% HCl in dioxane was added dropwise at 0° C. The resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N NaOH and extracted with CH2Cl2. The combined organic phases were concentrated under reduced pressure to get the title product as a very thick oil. 1H NMR (400 MHz, DMSO-d6): 8.00 (s, 1H), 7.58 (s, 2H), 3.78 (s, 2H), 2.18 (m, 1H), 0.50-0.35 (m, 4H).

후처리

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in MTBE
  3. addition20% HCl in dioxane was added dropwise at 0° C
  4. customThe resulting salt was collected
  5. washwashed with EtOAc
  6. extractionextracted with CH2Cl2
  7. concentrationThe combined organic phases were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0dd6ae224f0a451cae45a6181f20af8e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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