Cyanamide → HCID 19037038, compound

HRID 264831Notes

Reaction equation

HRID 264831 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH3:21])[CH:9]=[C:8]([C:10](=S)[NH:11][CH3:12])[C:7]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:6]=2[O:5]1.[I-].ClC1C=CC=C[N+]=1C.[N:31]#[C:32][NH2:33].[H-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:32]([NH:33][C:10]([C:8]1[C:7]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:6]=2[O:5][C:4]([CH2:3][O:2][CH3:1])([CH3:21])[CH:9]=1)=[N:11][CH3:12])#[N:31]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 24758Sodium hydrideHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19037033HCID 19037033, compound

Product 1

HCID 19037038HCID 19037038, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 158 mg of 2-methoxymethyl-N,2-dimethyl-6-nitro-2H-1-benzopyran-4-carbothioamide, 157 mg of 2-chloro-1-methylpyridinium iodide, 172 μl of triethylamine and 4 ml of dried tetrahydrofuran was refluxed with heating for 3 hours. The mixture was cooled to room temperature and to the resultant mixture were added 34 mg of cyanamide and 25 mg sodium hydride (60%) and the mixture was refluxed with heating for 4 hours. Ice water was added to the reaction product and it was extracted with ethyl acetate. An organic layer was washed with water and dried, and the solvent was distilled. The resultant residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 20 mg of N-cyano-2-methoxymethyl-N',2-dimethyl-6-nitro-2H-1-benzopyran-4-amidine with a melting point of 121°-125° C. by recrystallization from ethyl acetate.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 3 hours
  3. temperaturethe mixture was refluxed
  4. temperaturewith heating for 4 hours
  5. extractionwas extracted with ethyl acetate
  6. washAn organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled
  9. customThe resultant residue was purified

Sources & evidence

ORD record
ord-64f0544261754bb19d4ddcf8697d0847
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

Loading…