Water → HCID 20257592, compound

HRID 1583996Notes

Reaction equation

HRID 1583996 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:23]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH:27]=[CH:26][N:25]=[CH:24]1.O>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 792226-Chloronicotinic acidHCID 139528611H-Imidazole-1-octanamine

Product 1

HCID 20257592HCID 20257592, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.58 g of 6-chloronicotinic acid and 1.62 g of 1,1'-carbonyldiimidazole in 30 ml of tetrahydrofuran was stirred at room temperature for 3 hours. Then 1.95 g of 1H-imidazole-1-octanamine was added and the mixture was stirred at room temperature for 16 hours. The mixture was heated at reflux for 5 hours, 10 ml of water was added and heating was continued for one hour longer. The mixture was concentrated to remove tetrahydrofuran. Then 5 ml of 1N sodium hydroxide and dichloromethane was added. The mixture was shaken and the organic layer was separated, washed twice with water, dried over magnesium sulfate and filtered. The filtrate was concentrated and gave an oil. The oil was treated with diethyl ether to crystallize the desired compound as white crystals, mp 79°-81° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 5 hours
  4. temperatureheating
  5. waitwas continued for one hour
  6. concentrationThe mixture was concentrated
  7. customto remove tetrahydrofuran
  8. additionThen 5 ml of 1N sodium hydroxide and dichloromethane was added
  9. stirringThe mixture was shaken
  10. customthe organic layer was separated
  11. washwashed twice with water
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated
  15. customgave an oil
  16. customto crystallize the desired compound as white crystals, mp 79°-81° C.

Sources & evidence

ORD record
ord-028c98483b434c51a4f99e84536e721d
Source dataset
uspto-grants-1985_11
Patent number
US04555519

Reaction notes

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