Isopropanol → HCID 10998089, compound

HRID 470156Notes

Reaction equation

HRID 470156 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(OC(=O)C)(=O)C.[C:14]1([NH:20][C:21]([NH2:23])=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(O)C>C(O)(=O)C>[C:1]([CH2:3][C:4]([NH:23][C:21]([NH:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22])=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6145PhenylureaHCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acid2×

Product 1

HCID 10998089HCID 10998089, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

Cyanoacetic acid (28 g, 340 mmol) was taken in 20 ml acetic acid and 40 ml acetic anhydride (400 mmol), stirred at 50° C. until all cyanoacetic acid was solved. Phenyl urea (33.05 g, 247.5 mmol) was added and the mixture was stirred at 95° C. for 60 minute under LC-MS (Liquid Chromatography coupled with Mess Spectrometer) control of the reaction progress. After cooling down to room temperature, dilution with 20 ml 2-propanol and storing at 4° C. for 2 h, solids were separated by filtration, washed with cold 2-propanol and dried under high vacuum giving 40.06 g of white solids (82.6%).

Workup

  1. temperatureAfter cooling down to room temperature
  2. customsolids were separated by filtration
  3. washwashed with cold 2-propanol
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-299b2d1edf4c4511b5a0f93321d1d29d
Source dataset
uspto-grants-2014_01
Patent number
US08629272B2

Reaction notes

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