Benzo(d)thiazol-2-amine → N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide

HRID 2178215Notes

Reaction equation

HRID 2178215 reaction equation
[CH:1]1[N:5]=[CH:4][N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.NC1[S:15][C:16]2C=C[CH:20]=[CH:19][C:17]=2N=1>C(#N)C>[S:15]1[C:16]2[CH:17]=[CH:19][CH:20]=[CH:9][C:10]=2[N:11]=[C:12]1[NH:8][C:6]([N:3]1[CH:2]=[CH:1][N:5]=[CH:4]1)=[O:7]

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 59418727N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To CDI (1.6 g, 10 mmol) in acetonitrile (30 mL) was slowly added 2-aminobenzothiazole (1.0 g, 6.6 mmol) and allowed to stir at rt for 48 hours. The reaction mixture was filtered, washed with acetonitrile, and dried to provide 1.44 g (88%) of the desired product N-(benzo[d]thiazol-2-yl)-1-imidazole-1-carboxamide (1M): LC/MS (APCI): m/z 245.1 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-9999b25b842a468ea6e169b423f46654
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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