Benzoyl isothiocyanate → 1-Benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea

HRID 1809579노트

반응식

HRID 1809579 반응식
[O:1]([C:8]1[C:9]([NH2:21])=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:22]([NH:30][C:31]([NH:21][C:9]1[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:11][N:10]=1)=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 669951573-Phenoxy-5-(pyridin-2-ylthio)pyridin-2-amine

생성물 1

HCID 866410891-Benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea수율 88.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 125 mL flask was charged with 3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-amine (Example 34, Step A, 1.15 g, 3.89 mmol) and benzoyl isothiocyanate (0.699 g, 4.28 mmol) in THF (50 mL) and stirred at ambient temperature for 18 hours. The THF was removed in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and added dropwise to 100 mL of 9:1 hexanes:EtOAc. The solvent was decanted and the residue was dried to provide 1-benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea (1.57 g, 88.2% yield) as a yellow solid.

후처리

  1. customThe THF was removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  3. additionadded dropwise to 100 mL of 9:1 hexanes
  4. customThe solvent was decanted
  5. customthe residue was dried

출처 및 근거

ORD 기록
ord-5c284c46d08b40ebbd9b6b0fedaac801
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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