Dimethylformamide → HCID 86673130, compound

HRID 871844Notes

Reaction equation

HRID 871844 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[Cl:9][C:10]1(C(F)=O)[N:15]=[C:14]([NH:16][CH2:17][CH3:18])[CH:13]=[CH:12][NH:11]1.CN([CH:25]=[O:26])C>>[NH2:2][C:1]1[N:16]([CH2:17][CH3:18])[C:14]2[N:15]=[C:10]([Cl:9])[N:11]=[CH:12][C:13]=2[C:25](=[O:26])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7898CyanoacetamideHCID 24758Sodium hydride2×HCID 178463435HCID 178463435, compound

Product 1

HCID 86673130HCID 86673130, compoundYield 73.4%

Conditions

Temperature
3.5 °C

Procedure

To a solution, cooled to 2-5°C. on an ice bath, of 6.29 g (74.78 mmol) of cyanoacetamide in 140 mL of anhydrous DMF are added portionwise 5.98 g (149.55 mmol) of 60% sodium hydride. The mixture is stirred for 15 minutes at 2-5°C. and this suspension is then added rapidly to the solution of 14.5 g (71.22 mmol) of the acid fluoride prepared in step 2.5 in 155 mL of anhydrous DMF, precooled to 2-5°C. on an ice bath. The mixture is stirred overnight at room temperature and then cooled to 2-5°C., and 2.99 g (74.78 mmol) of 60% sodium hydride are added portionwise. The medium is stirred for 4 hours at room temperature, ice is then added slowly to destroy the excess hydride, and the reaction medium is poured into an ice-water mixture. The resulting mixture is acidified by adding aqueous 0.1 N HCl solution. The precipitate formed is isolated by filtration, rinsed with water and then dried in an oven, followed by rinsing with pentane. 14.0 g of expected product are finally obtained in the form of a pale orange solid. Yield=73.4%.

Workup

  1. customprecooled to 2-5°C. on an ice bath
  2. stirringThe mixture is stirred overnight at room temperature
  3. temperaturecooled to 2-5°C.
  4. stirringThe medium is stirred for 4 hours at room temperature
  5. additionice is then added slowly
  6. customto destroy the excess hydride
  7. additionthe reaction medium is poured into an ice-water mixture
  8. additionby adding aqueous 0.1 N HCl solution
  9. customThe precipitate formed
  10. customis isolated by filtration
  11. washrinsed with water
  12. customdried in an oven
  13. washby rinsing with pentane

Sources & evidence

ORD record
ord-2430d702f04a4748ab5ef3d25b94ee69
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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