Hydrochloric Acid → HCID 12968454, compound

HRID 1157402Notes

Reaction equation

HRID 1157402 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11]C(=O)C.C(O)C.Cl>O>[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4083933HCID 4083933, compound

Product 1

HCID 12968454HCID 12968454, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

58 mg (0.277 mmol) of N-(4-chloro-1H-benzimidazol-5-yl)acetamide (24-1) was suspended in a mixture of water, ethanol and concentrated HCl (0.06:1:0.4) for a total of 1 mL. The suspension was stirred and heated at 85° C. under nitrogen for 1 hour and after this time everything was soluble. The heat was turned off the solution was stirred overnight. The reaction was quenched with saturated NaHCO3. The pH was adjusted to 8 by adding solid NaHCO3 and Na2CO3. Extracted the reaction with ethyl acetate, dried, filtered and evaporated to recover the desired product 24-2. MS (M+1): measured 168.2; theoretical 167.0. 1H NMR (CD3OD): 6.75 (dd, 1H), 7.37 (d, 1H), 7.93 (s, 1H).

Workup

  1. stirringwas stirred overnight
  2. customThe reaction was quenched with saturated NaHCO3
  3. additionby adding solid NaHCO3 and Na2CO3
  4. extractionExtracted
  5. customthe reaction with ethyl acetate
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customto recover the desired product 24-2

Sources & evidence

ORD record
ord-50cae2dc47b24e4a85610be4e129b2d7
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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