Methyl iodide → HCID 22404729, compound

HRID 440701Notes

Reaction equation

HRID 440701 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]=[C:15]=[O:16])=[C:4]([F:17])[CH:3]=1.[H-].[Na+].[NH2:20]/[C:21](/[C:28]([F:31])([F:30])[F:29])=[CH:22]\[C:23](OCC)=[O:24].CI.[C:34](=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]2[C:23](=[O:24])[CH:22]=[C:21]([C:28]([F:31])([F:30])[F:29])[N:20]([CH3:34])[C:15]2=[O:16])=[C:4]([F:17])[CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 22404735HCID 22404735, compound

Product 1

HCID 22404729HCID 22404729, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method of Example 1, Step G, 4.0 grams (0.016 mole) of 5-chloro-3,4-dihydro-2,2-dimethyl-7-fluoro-2H-1-benzopyran-8-yl isocyanate was reacted with 1.0 gram (0.023 mole) of sodium hydride and 3.0 grams (0.017 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate in 150 mL of tetrahydrofuran. Subsequently, 4.5 grams (0.032 mole) of methyl iodide and 4.4 grams (0.032 mole) of potassium carbonate were reacted with the product of the first reaction, yielding 2.4 grams of 3-(5-chloro-3,4-dihydro-2,2-dimethyl- 7-fluoro-2H-1-benzopyran-8-yl)-1-methyl-6-trifluoromethyluracil, mp 132°-135° C. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-212e55230c9f413b9070cee89436b8f2
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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