Potassium Hydroxide → HCID 70980533, compound

HRID 1409339Notes

Reaction equation

HRID 1409339 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[OH-].[K+].[F:14][CH:15]([F:18])[CH2:16]I.[NH4+].[Cl-]>CN(C=O)C>[F:14][CH:15]([F:18])[CH2:16][N:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 38335651,1-Difluoro-2-iodoethane2×HCID 178469895HCID 178469895, compound

Product 1

HCID 70980533HCID 70980533, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-methyl-1H-imidazole-4-carboxylate (1.622 mmol, 250 mg) and KOH (2.432 mmol, 136 mg) were suspended in DMF (2 ml). 1,1-Difluoro-2-iodoethane (4.86 mmol, 934 mg) was added and the resulting mixture was stirred overnight at RT. During the stirring additional 0.3 ml of 1,1-difluoro-2-iodoethane was added to complete the reaction. Aqueous NH4Cl solution was added and the mixture was extracted three times with EtOAc. The combined organics were washed with water, dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.3 g of the title compound was obtained. Two isomers were obtained in the reaction and separated in later steps. Isomer 1: 1H-NMR (400 MHz, DMSO-d6): δ 1.28 (t, 3H), 2.33 (s, 3H), 4.25 (q, 2H), 4.45-4.58 (m, 2H), 6.23-6.53 (m, 1H), 7.80 (s, 1H). Isomer 2: 1H-NMR (400 MHz, DMSO-d6): δ 1.25 (t, 3H), 2.39 (s, 3H), 4.19 (q, 2H), 4.70-4.83 (m, 2H), 6.18-6.49 (m, 1H), 7.59 (s, 1H).

Workup

  1. customthe reaction
  2. extractionthe mixture was extracted three times with EtOAc
  3. washThe combined organics were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6b12e611c0044abd9074599d60ee2899
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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