2-Amino-6-methylbenzothiazole → N-(6-Methyl-1,3-benzothiazol-2-yl)-1H-imidazole-1-carboxamide

HRID 920130Notes

Reaction equation

HRID 920130 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[N:12]1([C:17](N2C=CN=C2)=[O:18])[CH:16]=[CH:15][N:14]=[CH:13]1>CN(C=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:9][C:17]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)=[O:18])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 173352-Amino-6-methylbenzothiazoleHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 59427382N-(6-Methyl-1,3-benzothiazol-2-yl)-1H-imidazole-1-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-methylbenzo[d]thiazol-2-amine (109, 328 mg, 2 mmol, Sigma-Aldrich) in DMF (5 mL) was added di(1H-imidazol-1-yl)methanone (110, 357 mg, 2.2 mmol, Sigma-Aldrich) at 0° C. Under vigorous stirring, the resulting reaction mixture was slowly allowed to warm to a temperature of about 25° C. over 14 h. A white precipitate formed. The precipitate was collected by filtration under reduced pressure, washed twice with EtOAc (10 mL for each wash), and dried under reduced pressure to provide 108 (yield >99%).

Workup

  1. customUnder vigorous stirring, the resulting reaction mixture
  2. customA white precipitate formed
  3. filtrationThe precipitate was collected by filtration under reduced pressure
  4. washwashed twice with EtOAc (10 mL for
  5. washeach wash), and
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-908c9f7f497e4013bcf80fd5870fb47a
Source dataset
uspto-grants-2016_03
Patent number
US09273043B2

Reaction notes

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