Potassium Hydroxide → 2-(1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole

HRID 1244296

Reaction equation

HRID 1244296 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:27][C:26]=1[NH:37][C:38]([C:40]1[NH:41][CH:42]=[CH:43][N:44]=1)=[S:39].[OH-].[K+]>O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+6]>[NH:44]1[CH:43]=[CH:42][N:41]=[C:40]1[C:38]1[S:39][C:27]2[C:28]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[C:26]=2[N:37]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 87949Lawesson's reagentHCID 865949991H-imidazole-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide

Product 1

HCID 1354097702-(1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole

Reagents, catalysts & solvents 2

HCID 11963580Ferrate(4-), hexakis(cyano-C)-, tetrapotassium, (OC-6-11)-CatalystHCID 962WaterSolvent

Procedure

According to scheme 1, to a suspension of a imidazole-2-carboxylic acid (X) was added CDI (1,1′-carbonyl-diimidazole) and stirred at ambient temperature for about 1 h. Then the mixture was refluxed and cooled to ambient temperature. 2-Methoxy-5-morpholin-4-yl-phenylamine (for R1=morpholinyl, IX) was added and the reaction mixture was heated to reflux for about 16 h. After workup 1H-imidazole-2-carboxylic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (XI) was obtained, which was then treated with the Lawesson reagent. The reaction mixture was then heated to reflux for about 22 h. The obtained 1H-imidazole-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (II) was taken up in water and treated with KOH and potassium hexacyano ferrate to give 2-(1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole (Ia for R1=morpholinyl).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for about 22 h

Sources & evidence

ORD record
ord-da81082761b14715b9607103c7d8b5d2
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Linked notes

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