Sodium Bicarbonate → HCID 178497569, compound

HRID 2365608Notes

Reaction equation

HRID 2365608 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:14]1([C:13]2[NH:12][C:3]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=3[N:1]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59625820HCID 59625820, compound

Product 1

HCID 178497569HCID 178497569, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 810 mg (3.0 mmol) of methyl 3-amino-2-benzoylamino-benzoate 9y in 15 ml acetic acid was heated to 125° C. for 1.5 h. The reaction was cooled and poured into ice/water. The aqueous layer was made basic with NaHCO3 and extracted with CH2Cl2. The organic solution was dried over Na2SO4 and evaporated to give 540 mg (71%) of methyl 2-phenyl-1H-benzo[d]imidazole-7-carboxylate, 9z. MS m/z (M+H+) 253.2

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-fd662db48f054b17b8b4395bb4ff17ac
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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