Pyridine → p-Toluenesulfonamide, N-benzyl-

HRID 1765929

반응식

HRID 1765929 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH2:18]([NH:25][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7504Benzylamine

생성물 1

HCID 95801p-Toluenesulfonamide, N-benzyl-수율 79.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of P-HOBT 6 (1.01 g, 0.49 mmol) in CH2Cl2 (5 mL) was added p-toluenesulfonyl chloride (0.280 g, 1.47 mmol, 3.00 equiv.) and pyridine (0.155 g, 0.160 mL, 1.98 mmol, 4.04 equiv.). The suspension was subsequently rocked for 60 minutes at 25° C. The polymer was then filtered and washed with CH2Cl2 (3×5 mL), MeCN (3×5 mL), and MeOH (3×5 mL). The polymer was re-suspended in CH2Cl2 (5 mL), followed by the addition of benzylamine (0.026 g, 0.027 mL, 0.24 mmol, 0.49 equiv. based on P-HOBT 6). The suspension was rocked at 25° C. for 2 h. The polymer was then filtered and washed with CH2Cl2 (2×5 mL). The filtrate and washings were combined and concentrated to yield 0.050 g (77%) of N-benzyl-p-toluenesulfonamide as a light yellow crystalline solid.

후처리

  1. filtrationThe polymer was then filtered
  2. washwashed with CH2Cl2 (3×5 mL), MeCN (3×5 mL), and MeOH (3×5 mL)
  3. waitThe suspension was rocked at 25° C. for 2 h
  4. filtrationThe polymer was then filtered
  5. washwashed with CH2Cl2 (2×5 mL)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4e84622bf9c042f69016e7791b8649ac
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229835B2

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