Formic Acid → HCID 15034981, compound

HRID 1090225Notes

Reaction equation

HRID 1090225 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[N:35]1([CH2:40][CH2:41][CH2:42][NH2:43])[CH:39]=[CH:38][N:37]=[CH:36]1>O1CCCC1.O>[N:35]1([CH2:40][CH2:41][CH2:42][NH:43][CH:5]=[O:7])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 787361H-Imidazole-1-propanamineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 15034981HCID 15034981, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

12.3 ml of acetic anhydride was cooled below 0° C. and treated dropwise with 6.1 ml of 98% formic acid, keeping the reaction temperature below 0° C. by external cooling. The mixture was then slowly warmed, and kept at 50° C.-60° C. for two hours. 10 ml of tetrahydrofuran was added, and the solution of acetic formic anhydric cooled to -20° C. A solution of 6.2 g of 3-(1H-imidazol-l-yl)propanamine in 20 ml of tetrahydrofuran was then added dropwise, keeping the temperature below -10° C. The reaction mixture was allowed to come to room temperature, 10 ml of water was added, and the mixture taken to dryness in vacuo. Distillation of the viscous residue at 195° C.-200° C. gave 6.2 g of N-(3-(1H-imidazol-l-yl)propyl)formamide. This was reduced to N-methyl-3-(1H-imidazol-l-yl)propylamine by the use of borane dimethylsulfide in refluxing tetrahydrofuran.

Workup

  1. customthe reaction temperature below 0° C.
  2. temperatureThe mixture was then slowly warmed
  3. customthe temperature below -10° C
  4. customto come to room temperature
  5. distillationDistillation of the viscous residue at 195° C.-200° C.

Sources & evidence

ORD record
ord-1715294bc1224094907545e09e8aea48
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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