p-Toluenesulfonyl azide → HCID 73213267, 화합물

HRID 2381784노트

반응식

HRID 2381784 반응식
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.S([N:28]=[N+:29]=[N-])(C1C=CC(C)=CC=1)(=O)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.[OH-].[Na+]>[N:1]([C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1)=[N+:28]=[N-:29]

참가 물질

6

반응물 2

HCID 13661p-Toluenesulfonyl azideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

생성물 1

HCID 73213267HCID 73213267, 화합물수율 63%

시약·촉매·용매 3

HCID 5963Benzyltrimethylammonium chloride촉매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (1.20 g, 4.86 mmol), tosyl azide (1.91 g, 9.71 mmol) and benzyl trimethylammonium chloride (0.05 g, 0.27 mmol) in dichloromethane (21 mL) and 40% aqueous sodium hydroxide solution (11 mL) was stirred at ambient temperature for 18 h. The reaction mixture was extracted with dichloromethane (100 mL). The separated organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.83 g, 63%): MS (ES−) m/z 272.2 (M−1).

후처리

  1. extractionThe reaction mixture was extracted with dichloromethane (100 mL)
  2. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:4)

출처 및 근거

ORD 기록
ord-0fab73d4ddca403b9bd0a223381784e9
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258160B2

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