Ethyl chloroformate → HCID 22996008, compound

HRID 1167466Notes

Reaction equation

HRID 1167466 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10]2)=[C:6]([F:8])[CH:7]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>N1C=CC=CC=1>[CH2:20]([O:19][C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10]2)=[C:6]([F:8])[CH:7]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 229961405-Amino-2-(3-cyano-1-pyrrolyl)fluorobenzene

Product 1

HCID 22996008HCID 22996008, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-2-(3-cyano-1-pyrrolyl)fluorobenzene (4.6 g, 22.9 mmol) was stirred in dry pyridine (50 ml) 0°. Ethyl chloroformate (2.66 g, 24.5 mmol) was added, and stirring continued for 20 minutes at the same temperature before allowing the temperature to rise to ambient over 2 hours. Solvent was evaporated, the residue treated with iced water (50 ml), filtered off, and dried. Crystallisation of the crude product from ethanol (200 ml) gave the title product (4.9 g) mp 188-190°.

Workup

  1. waitto ambient over 2 hours
  2. customSolvent was evaporated
  3. additionthe residue treated with iced water (50 ml)
  4. filtrationfiltered off
  5. customdried
  6. customCrystallisation of the crude product from ethanol (200 ml)

Sources & evidence

ORD record
ord-4eaa8661df40433db41887d4580355e4
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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