Hydrochloric Acid → HCID 67326095, compound

HRID 871886Notes

Reaction equation

HRID 871886 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[CH3:9][S:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([C:24](F)=[O:25])=[CH:13][N:12]=1.Cl>CN(C=O)C>[NH2:2][C:1]1[N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]2[N:16]=[C:11]([S:10][CH3:9])[N:12]=[CH:13][C:14]=2[C:24](=[O:25])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydride2×HCID 89106744HCID 89106744, compound

Product 1

HCID 67326095HCID 67326095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1.0 g (11.96 mmol) of cyanoacetamide in 17 mL of anhydrous DMF, cooled to 0-5°C., is added 0.96 g (23.93 mmol) of 60% NaH. After the addition, the mixture is stirred for 10 minutes at room temperature and then cooled again on an ice-water bath, and a solution of 3.0 g the acid fluoride (11.39 mmol) prepared in step 20.3 in 17 mL of anhydrous DMF is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is cooled on an ice-water bath, and 0.48 g (11.96 mmol) of 60% NaH is added. The reaction mixture is stirred for 5 hours at room temperature and then poured into ice-cold aqueous 0.5 N HCl solution. The precipitate formed is isolated by filtration, rinsed with water, drained by suction and then dried in an oven. 3.44 g of a yellow solid mainly composed of the expected product in non-cyclized form are obtained.

Workup

  1. additionAfter the addition
  2. temperaturecooled again on an ice-water bath
  3. stirringThe reaction mixture is stirred at room temperature overnight
  4. temperatureThe reaction mixture is cooled on an ice-water bath
  5. stirringThe reaction mixture is stirred for 5 hours at room temperature
  6. customThe precipitate formed
  7. customis isolated by filtration
  8. washrinsed with water
  9. customdried in an oven
  10. customare obtained

Sources & evidence

ORD record
ord-6caa07eb86a44270b704d9e909367f13
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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