1,1'-Carbonyldiimidazole → HCID 86010015, compound

HRID 1244295Notes

Reaction equation

HRID 1244295 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:25][C:24]=1[NH2:35]>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[CH:25][C:24]=1[NH:35][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:8]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5743211H-Imidazole-2-carboxylic acidHCID 113677782-Methoxy-5-morpholinoaniline

Product 1

HCID 86010015HCID 86010015, compound

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. temperatureThen the mixture was refluxed
  2. temperaturecooled to ambient temperature
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for about 16 h

Sources & evidence

ORD record
ord-bed39b4ce3734a5fab4aab942ed412d4
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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