Ammonia → HCID 21194011, compound

HRID 1067474Notes

Reaction equation

HRID 1067474 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11](O)=O)=[CH:5][CH:4]=1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][NH:27][C:28]1[CH:44]=[CH:43][C:31]([CH2:32][N:33]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[N:35]=[C:34]2[CH3:42])=[CH:30][C:29]=1[NH2:45].N>O1CCCC1.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[N:27]([CH3:26])[C:28]3[CH:44]=[CH:43][C:31]([CH2:32][N:33]4[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=5[N:35]=[C:34]4[CH3:42])=[CH:30][C:29]=3[N:45]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 817965N-(4-Cyanophenyl)glycineHCID 21193883HCID 21193883, compound

Product 1

HCID 21194011HCID 21194011, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.94 g (11.0 mmol) of N-(4-cyanophenyl)-glycine and 1.78 g (11.0 mmol) of carbonyldiimidazole is refluxed in 80 ml of absolute tetrahydrofuran for 15 minutes. After the addition of 2.7 g (10.46 mmol) of 1-(4-methylamino-3-aminobenzyl)-2-methyl-benzimidazole the mixture is refluxed for a further 16 hours. Then the solution is evaporated to dryness, the residue is mixed with 80 ml glacial acetic acid and refluxed for 1 hour. It is then evaporated to dryness once more, the residue thus obtained is mixed with 50 ml of water and made alkaline with conc. ammonia (about pH 10). The product which crystallises out is suction filtered, washed with a little water and dried.

Workup

  1. temperatureis refluxed for a further 16 hours
  2. customThen the solution is evaporated to dryness
  3. additionthe residue is mixed with 80 ml glacial acetic acid
  4. temperaturerefluxed for 1 hour
  5. customIt is then evaporated to dryness once more
  6. customthe residue thus obtained
  7. customThe product which crystallises out is suction
  8. filtrationfiltered
  9. washwashed with a little water
  10. customdried

Sources & evidence

ORD record
ord-6a46331b80e74d37bbfb3cf48d1b64c4
Source dataset
uspto-grants-2001_06
Patent number
US06248770B1

Reaction notes

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