Acetic Anhydride → HCID 53761108, compound

HRID 224586Notes

Reaction equation

HRID 224586 reaction equation
[C:1](CC(O)=O)#[N:2].[CH:7]1([NH:12][C:13]([NH:15][CH3:16])=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(O[C:21](=[O:23])[CH3:22])(=O)C>>[NH2:2][C:1]1[N:12]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:13](=[O:14])[N:15]([CH3:16])[C:21](=[O:23])[CH:22]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 13428331N-Cyclopentyl-N′-methylurea

Product 1

HCID 53761108HCID 53761108, compound

Conditions

Temperature
70 °C

Procedure

To a solution of 47 g (0.55 mol) of cyanoacetic acid and 150 ml of acetic anhydride was added 73.1 g (0.51 mol) of 1-cyclopentyl-3-methylurea (XX). The solution was stirred at 70° C. for two hours. It was then evaporated and the residual oil (XXI) was dissolved in 400 ml of ethanol and 400 ml of water and 110 ml of 5 N NaOH was added in portions until the pH was over 7, under which the solution was boiled. It was then partly evaporated and crystals were filtered off. These crystals were a mixture of XX (~30%) and XXII (~70%) which was used for synthetizing XXII. Yield 30.8 g. NMR.

Workup

  1. customIt was then evaporated
  2. dissolutionthe residual oil (XXI) was dissolved in 400 ml of ethanol
  3. addition400 ml of water and 110 ml of 5 N NaOH was added in portions until the pH
  4. customIt was then partly evaporated
  5. filtrationcrystals were filtered off
  6. additiona mixture of XX (~30%) and XXII (~70%) which

Sources & evidence

ORD record
ord-bfeaccb968cd4c9489b327963b0c9304
Source dataset
uspto-grants-1980_11
Patent number
US04233303

Reaction notes

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