Cyanoacetamide → HCID 178510174, compound

HRID 1599017Notes

Reaction equation

HRID 1599017 reaction equation
C[O-].[Na+].[CH:4](OCC)=O.[F:9][CH2:10][C:11]([O:13]CC)=O.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17]>CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>[OH:20][C:19]1[C:18]([C:16]#[N:17])=[CH:4][C:10]([F:9])=[C:11]([OH:13])[N:21]=1

Participants

9

Reactant 4

HCID 7898CyanoacetamideHCID 8025Ethyl formate2×HCID 9988Ethyl fluoroacetate4×HCID 10942334Sodium Methoxide

Product 1

HCID 178510174HCID 178510174, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

A 300 gallon reaction vessel was charged with 300 L of toluene, blanketed with nitrogen and 30.6 kg of sodium methoxide was added. This was followed by 62.6 kg of ethyl formate. The temperature was maintained below 30° C. Ethyl fluoroacetate, 30 kg, was added to the mixture. (Extreme caution must be used when working with ethyl fluoroacetate. Ethyl fluoroacetate is highly toxic). The ethyl formate and ethyl fluoroacetate were metered to maintain the temperature at about 30° C. The reaction mixture was allowed to stir for 3 to 5 hours and formed a suspension. The suspension was allowed to cool to 5°-10° C. and cyanoacetamide, 71.4 kg, was added. This formed a thick suspension which was diluted with about 300 L of methanol, allowed to warm to room temperature (about 20° C.) and stirred for an additional 12-16 hours. Glacial acetic acid, 35.6 L, and water, 200 L, were added to the suspension. The suspension was centrifuged to separate the product. The product was collected and dried. The title compound, M. W. 154.10, had a purity of 95%, by HPLC, and m.p. 135°-140° C.

Workup

  1. customA 300 gallon reaction vessel
  2. additionwas added
  3. temperatureThe temperature was maintained below 30° C
  4. customformed a suspension
  5. temperatureto cool to 5°-10° C.
  6. customThis formed a thick suspension which
  7. temperatureto warm to room temperature (about 20° C.)
  8. stirringstirred for an additional 12-16 hours
  9. customto separate the product
  10. customThe product was collected
  11. customdried

Sources & evidence

ORD record
ord-5b66432f1a874e0d81a0754ea9dab544
Source dataset
uspto-grants-1998_04
Patent number
US05739342

Reaction notes

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