p-Toluenesulfonyl azide → HCID 73213267, compound

HRID 2381784Notes

Reaction equation

HRID 2381784 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

HCID 73213267HCID 73213267, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0fab73d4ddca403b9bd0a223381784e9
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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