Cyanamide → HCID 19037076, compound

HRID 264845Notes

Reaction equation

HRID 264845 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:6]=1)=S.[I-].ClC1C=CC=C[N+]=1C.[N:32]#[C:33][NH2:34].[H-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:33]([NH:34][C:3]([C:5]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:6]=1)=[N:2][CH3:1])#[N:32]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 24758Sodium hydrideHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19037011N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide

Product 1

HCID 19037076HCID 19037076, compoundYield 6.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 200 mg of N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide, 192 mg of 2-chloro-1-methylpyridinium iodide, 209 μl of triethylamine and 5 ml of dried tetrahydrofuran was refluxed with heating for 2 hours and further cooled to room temperature. 42 mg of cyanamide and 30 mg of sodium hydride (60%) were added therein and the reaction mixture was refluxed with heating for 2 hours. Ice water was added therein and the resultant mixture was extracted with methylene chloride. An organic layer was washed with water and dried, and the solvent was distilled. The obtained residue was purified according to silica gel column chromatography (developing solution, CH2Cl2) and recrystallized by a mixed solvent of ethyl acetate and hexane to obtain 14 mg of N-cyano-N'-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-amidine with a melting point of 293°-294° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 2 hours
  3. temperaturethe reaction mixture was refluxed
  4. temperaturewith heating for 2 hours
  5. extractionthe resultant mixture was extracted with methylene chloride
  6. washAn organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled
  9. customThe obtained residue was purified
  10. customrecrystallized by a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e025dc45fb6444468a0d988767ba7785
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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