Hydrochloric Acid → HCID 19036999, compound

HRID 264856Notes

Reaction equation

HRID 264856 reaction equation
[F:1][C:2]([F:25])([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=[C:12]([C:20](=S)[NH:21][CH3:22])[C:11]=2[CH:24]=1)[C:3]([F:6])([F:5])[F:4].C(I)C.[H-].[Na+].[N:31]#[C:32][NH2:33].Cl>O1CCCC1>[C:32]([NH:33][C:20]([C:12]1[C:11]2[CH:24]=[C:7]([C:2]([F:25])([F:1])[C:3]([F:4])([F:5])[F:6])[CH:8]=[CH:9][C:10]=2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=1)=[N:21][CH3:22])#[N:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 9864CyanamideHCID 24758Sodium hydride2×HCID 19037031HCID 19037031, compound

Product 1

HCID 19036999HCID 19036999, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.14 g of 6-pentafluoroethyl-2,2-bis(fluoromethyl)-N-methyl-2H-1-benzopyran-4-carbothioamide, 0.31 g of ethyl iodide, 0.017 g of sodium hydride and 5 ml of tetrahydrofuran was refluxed with heating for 45 minutes. To the reaction mixture were added 0.081 g of cyanamide and 0.017 g of sodium hydride and the resultant mixture was refluxed with heating for 22 hours. To the reaction mixture was added a small amount of hydrochloric acid and the mixture was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (developing solution, ethyl acetate:hexane=1:1) to obtain 0.07 g of N-cyano-6-pentafluoroethyl-2,2-bis(fluoromethyl)-N'-methyl-2H-1-benzopyran-4-amidine with a melting point of 178°-179° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 45 minutes
  3. temperaturewith heating for 22 hours
  4. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93d992791ef84872af548a4c0081a0d4
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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