Ammonia → HCID 20145200, compound

HRID 648645Notes

Reaction equation

HRID 648645 reaction equation
C(C1NC=CN=1)(C1[NH:4]C=CN=1)=O.[N:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]([CH:27]([C:37]([NH2:39])=[O:38])[C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=O)=[CH:30][CH:29]=2)[CH3:26])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.N>N1C=CC=CC=1>[N:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]([CH:27]([C:37]([NH2:39])=[O:38])[C:28]2[CH:36]=[CH:35][C:31]([C:32]([NH2:4])=[O:34])=[CH:30][CH:29]=2)[CH3:26])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 20145110HCID 20145110, compound

Product 1

HCID 20145200HCID 20145200, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An amount of 2.3 gm (0.0142 mol) of carbonyl diimidazole was mixed with 4.76 gm (0.013 mol) of 4-[(1-(2-piperidinophenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid in 60 ml of absolute pyridine, and the mixture was subsequently heated for 45 minutes to 50° C. After cooling in a carbon dioxide/methanol bath, 7 ml of liquid ammonia were added, and the mixture was heated for 20 hours to 80° C. in an autoclave. Subsequently the reaction mixture was cooled and evaporated in vacuo. The residue was dissolved in 50 ml of hot methanol, 200 ml of water were added, and the mixture was allowed to stand overnight. The crystalline precipitate was recovered by suction filtration and recrystallized from methanol by addition of activated charcoal.

Workup

  1. temperaturethe mixture was subsequently heated for 45 minutes to 50° C
  2. temperatureAfter cooling in a carbon dioxide/methanol bath
  3. temperaturethe mixture was heated for 20 hours to 80° C. in an autoclave
  4. temperatureSubsequently the reaction mixture was cooled
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in 50 ml of hot methanol
  7. addition200 ml of water were added
  8. filtrationThe crystalline precipitate was recovered by suction filtration
  9. customrecrystallized from methanol by addition of activated charcoal

Sources & evidence

ORD record
ord-a905468fa5ca43788d24eddbb4e3da5f
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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