Tetrahydrofuran → HCID 53986092, compound

HRID 1599991Notes

Reaction equation

HRID 1599991 reaction equation
[CH2:1]([NH:4][C:5]#[N:6])[CH:2]=[CH2:3].[Cl:7][C:8](=[CH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:23]([Cl:24])=[C:22]([O:25][CH:26]([F:28])[F:27])[N:21]([CH3:29])[N:20]=2)[C:16]([Cl:30])=[CH:15][C:14]=1[Cl:31])[C:9](Cl)=[O:10].[O:32]1CCCC1>>[CH2:1]([N:4]([C:5]([NH2:6])=[O:32])[C:9](=[O:10])[C:8]([Cl:7])=[CH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:23]([Cl:24])=[C:22]([O:25][CH:26]([F:28])[F:27])[N:21]([CH3:29])[N:20]=2)[C:16]([Cl:30])=[CH:15][C:14]=1[Cl:31])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 12295222Cyanamide, 2-propenyl-HCID 53725594HCID 53725594, compound

Product 1

HCID 53986092HCID 53986092, compound

Conditions

Temperature
55 °C

Procedure

0.36 g (4.4 mmol) of allylcyanamide were added to a suspension of 2 g (4.4 mmol) of 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)Propenoyl chloride and 0.8 g (5.8 mmol) of potassium carbonate(ground) in 50 ml of tetrahydrofuran. The reaction mixture was stirred at 50 to 60° C. for 5 hours and then concentrated. The residue was taken up in ethyl acetate, after which the organic phase was washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by means of column chromatography on silica gel (eluent: ethyl acetate) followed by crystallization from diisopropyl ether. Yield: 0.2 g.

Workup

  1. concentrationconcentrated
  2. washafter which the organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by means of column chromatography on silica gel (eluent: ethyl acetate)
  6. customfollowed by crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-91bc213efd4b4ce8b0f2c6135cf38971
Source dataset
uspto-grants-1998_04
Patent number
US05744426

Reaction notes

Loading…