Ammonia → HCID 66758968, compound

HRID 1402802Notes

Reaction equation

HRID 1402802 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]3[C:12](=[O:13])[CH2:11][CH:10]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:9][C:7]3=[N:8][C:4]=2[CH:3]=1.[Cl:22]C1C=CC2N=C3CC(C4C=CC=CC=4)CC(=O)N3C=2C=1.[NH3:43]>O1CCOCC1.O.CC(C)=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:43]=[C:7]([CH2:9][CH:10]([C:14]3[CH:19]=[CH:18][C:17]([Cl:22])=[CH:16][CH:15]=3)[CH2:11][C:12]([NH2:6])=[O:13])[NH:8][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 66759663HCID 66759663, compoundHCID 66760151HCID 66760151, compound

Product 1

HCID 66758968HCID 66758968, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 1:1-mixture of 7-chloro-3-phenyl-3,4-dihydropyrido[1,2-a]-benzimidazol-1(2H)-one and 8-chloro-3-phenyl-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one (222 mg)—see example 1.27.1—was dissolved in 1,4-dioxane (3 ml) at reflux temperature. A 25% solution of ammonia in water (2 ml) was added to give a light red solution. Refluxing was continued for 1 h. All volatiles were removed at the water aspirator to leave a light red oil, which was dissolved in acetone (3 ml). Soon precipitation occurs and the solid is isolated by suction filtration and washed with acetone. After drying in vacuo 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)-butyramide (120 mg) is obtained as colourless solid.

Workup

  1. temperatureat reflux temperature
  2. customto give a light red solution
  3. temperatureRefluxing
  4. customAll volatiles were removed at the water
  5. customto leave a light red oil, which
  6. customSoon precipitation
  7. customthe solid is isolated by suction filtration
  8. washwashed with acetone
  9. dry with materialAfter drying in vacuo 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)-butyramide (120 mg)
  10. customis obtained as colourless solid

Sources & evidence

ORD record
ord-8ff29fc19e854ab3a0f1d99cf5225453
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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