Carbamic acid, ethyl ester → Diethyl(4-Cyano-2-fluorophenyl)methylenedicarbamate

HRID 927209Notes

Reaction equation

HRID 927209 reaction equation
[Cl-].[Ca+2].[Cl-].[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[CH:13]=O)[C:8]#[N:9].[C:15](=[O:20])([O:17][CH2:18][CH3:19])[NH2:16]>>[C:8]([C:7]1[CH:10]=[CH:11][C:12]([CH:13]([NH:16][C:15](=[O:20])[O:17][CH2:18][CH3:19])[NH:16][C:15](=[O:20])[O:17][CH2:18][CH3:19])=[C:5]([F:4])[CH:6]=1)#[N:9]

Participants

4

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 27831503-Fluoro-4-formylbenzonitrileHCID 5284359Calcium Chloride

Product 1

HCID 90327812Diethyl(4-Cyano-2-fluorophenyl)methylenedicarbamate

Conditions

Temperature
150 °C

Procedure

In a three-necked round bottom flask equipped with a drying tube filled with calcium chloride and an inlet for nitrogen, 3-fluoro-4-formylbenzonitrile (5.00 g, 33.5 mmol) and ethyl carbamate (6.57 g, 73.7 mmol) are heated at 150° C. The flask is being purged with a flow of nitrogen, and concentrated sulfuric acid (200 μL) is added drop by drop within 10 min. The mixture is heated at 150° C. for 6 h and then cooled at room temperature. The mixture is ground, treated with water (400 mL) and then stirred for 3 h. The precipitate is filtered and dried. Yield: 6.50 g; ESI mass spectrum: [M+Na]+=332; Retention time HPLC: 0.58 min (Z011_S03).

Workup

  1. customIn a three-necked round bottom flask equipped with a drying tube
  2. customThe flask is being purged with a flow of nitrogen, and concentrated sulfuric acid (200 μL)
  3. additionis added drop by drop within 10 min
  4. temperatureThe mixture is heated at 150° C. for 6 h
  5. temperaturecooled at room temperature
  6. additiontreated with water (400 mL)
  7. filtrationThe precipitate is filtered
  8. customdried
  9. custom0.58 min (Z011_S03)

Sources & evidence

ORD record
ord-ae981ff899e6427e99cb0663d0f67da1
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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