Ammonia → 1-Phenylcyclopropanecarboxamide

HRID 1685316Notes

Reaction equation

HRID 1685316 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2([C:14]([OH:16])=O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH3:17]>C1(C)C=CC=CC=1.CN(C=O)C.Cl>[C:5]1([C:11]2([C:14]([NH2:17])=[O:16])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 2922171-PhenylcyclopropanecarboxamideYield 95%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Thionyl chloride (0.225 mL, 3.08 mmol) was slowly added to a solution of 1-phenylcyclopropanecarboxylic acid (0.50 g, 3.08 mmol) in toluene (10 mL) and DMF (0.3 mL). The reaction was then heated at reflux for 2 hours, then cooled down to 23° C. and treated (slow addition) with a solution of ammonia (2M in methanol, 10 mL). The reaction was then stirred at 23° C. overnight. The reaction was then diluted with hydrochloric acid (1N) and extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (0.474 g, 95%) as a solid which was used as such in the next reaction. 1H NMR (400 MHz, CDCl3) δ: 1.11 (2H, q, J=3.79 Hz), 1.60-1.66 (2H, m), 5.34 (1H, br s), 5.91 (1H, br s), 7.31-7.41 (3H, m), 7.43-7.47 (2H, m). HPLC ret. time (Condition B): 1.225 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 2 hours
  3. additiontreated
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7fd41ec2300e492cad7e6819c422c10c
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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