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Formamidine acetate → 7-Chloro-6-phenylamino-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 32034
Notes
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Reaction equation

HRID 32034 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([Cl:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:21](O)(=O)C.C(N)=N>CCO.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:6]([Cl:12])[C:7]2[N:11]=[CH:21][NH:10][C:8]=2[CH:9]=1)=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 858681984,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester

Product 1

HCID 865990177-Chloro-6-phenylamino-3H-benzoimidazole-5-carboxylic acid methyl esterYield 100.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester 6b (0.32 g, 1.09 mmol) and formamidine acetate (72 mg, 1.64 mmol) in EtOH (36 mL) are heated, with stirring, to 80° C. After 44 hours, the reaction mixture is cooled to room temperature and diluted with EtOAc and washed with water (3×), saturated NaHCO3, and brine. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure to give 0.33 g (99%) clean desired product as a solid. MS APCI (+) m/z 302.3 (M+1) detected.

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. washwashed with water (3×), saturated NaHCO3, and brine
  3. dry with materialThe combined organic extracts are dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f81764e602c5428f9da52d9dfb3b0aa3
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425637B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes