Acetic Acid → HCID 12035495, compound

HRID 1634244Notes

Reaction equation

HRID 1634244 reaction equation
[C:1]([C:3]1[C:11]2[N:10]([CH3:12])[C:9]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])=[N:8][C:7]=2[CH:6]=[CH:5][C:4]=1[C:22]1(C(OCC)=O)[CH2:26][CH2:25][CH2:24][C:23]1=O)#[N:2].C(O)(=[O:35])C.OS(O)(=O)=O>O>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[NH:13][C:9]1[N:10]([CH3:12])[C:11]2[C:3]3[C:1](=[O:35])[NH:2][C:26]4[CH2:25][CH2:24][CH2:23][C:22]=4[C:4]=3[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 23502954HCID 23502954, compound

Product 1

HCID 12035495HCID 12035495, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of the above benzimidazole (195 mg, 0.41 mmol) in a 1:1:1 mixture of water, acetic acid and H2SO4 (1.5 mL) was heated at 100° C. for 3 h. The reaction mixture was cooled and diluted with water. The precipitate was collected and washed with water. The collected yellow solid was purified by chromatography on SiO2 in CH2Cl2 /MeOH (20:1) to give the title compound (70 mg, 43%) as a light yellow solid. Mp>300° C. (dec.), MS (CI) m/z 399 (M++H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe precipitate was collected
  3. washwashed with water
  4. customThe collected yellow solid was purified by chromatography on SiO2 in CH2Cl2 /MeOH (20:1)

Sources & evidence

ORD record
ord-7ca31b904ad34633b7a9e56e0028112c
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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