Bis-(1H-imidazol-2-YL)-methanone → HCID 178521403, compound

HRID 2248142Notes

Reaction equation

HRID 2248142 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[O:17][CH2:18][C:19](O)=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1>O1CCCC1>[NH:39]1[C:38]([NH:37][C:19](=[O:20])[CH2:18][O:17][C:16]2[CH:22]=[CH:23][CH:24]=[C:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH:15]=2)=[N:42][N:41]=[N:40]1

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 19805551HCID 19805551, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178521403HCID 178521403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution at 40° C. of 13.1 g. (39.8 mMol) 3-[2-(benzyloxycarbonylamino)-ethyl]-phenoxyacetic acid and 130 ml. anhydrous tetrahydrofuran are added 6.48 g. (39.9 mMol) carbonyl-bis-imidazole, followed by stirring for 30 minutes at 40° C. 3.39 g. (39.9 mMol) anhydrous 5-aminotetrazole are then added thereto and allowed to react for 18 hours at 60° C. After distilling off the tetrahydrofuran, there is obtained a colourless oil which is stirred with 130 ml. 2N hydrochloric acid, crystallisation thereby taking place. The crystals are filtered off with suction, triturated with dilute hydrochloric acid, again filtered off with suction and washed with water. After drying in a vacuum at 80° C. over potassium hydroxide and recrystallising from nitromethane, there are obtained 12.7 g. (50.5% of theory) of the desired product; m.p. 164°-167° C.

Workup

  1. customat 40° C.
  2. customto react for 18 hours at 60° C
  3. distillationAfter distilling off the tetrahydrofuran
  4. customthere is obtained a colourless oil which
  5. stirringis stirred with 130 ml
  6. custom2N hydrochloric acid, crystallisation
  7. filtrationThe crystals are filtered off with suction
  8. customtriturated with dilute hydrochloric acid
  9. filtrationagain filtered off with suction
  10. washwashed with water
  11. dry with materialAfter drying in a vacuum at 80° C. over potassium hydroxide
  12. customrecrystallising from nitromethane, there
  13. customare obtained 12.7 g

Sources & evidence

ORD record
ord-f0b21cb6078e4b74b98c28ec5d50d713
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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