Methylamine → HCID 19037060, compound

HRID 264849Notes

Reaction equation

HRID 264849 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[CH:10]=[C:9]([C:18](O)=[O:19])[C:8]=2[CH:21]=1)([O-:3])=[O:2].[C:22](N1C=CN=C1)([N:24]1C=CN=C1)=O.CN.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:22][NH:24][C:18]([C:9]1[C:8]2[CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:17][C:11]2([CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)[CH:10]=1)=[O:19]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 19037059HCID 19037059, compound

Product 1

HCID 19037060HCID 19037060, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 80 mg of 6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-carboxylic acid and 7 ml of tetrahydrofuran was added 80 mg of 1,1'-carbonyldiimidazole with stirring under ice-cooling and the mixture was stirred for 1 hour. 0.7 ml of 40% methylamine (methanol solution) was added therein and the mixture was stirred under ice-cooling for 1 hour and then at room temperature for 20 hours. An aqueous potassium carbonate solution was added therein and the reaction mixture was extracted with methylene chloride. An organic layer was washed with water and dried, and the solvent was distilled. The residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) and further recrystallized by a mixed solvent of ethyl acetate and hexane to obtain 28 mg of N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-carboxamide with a melting point of 208°-209° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hour
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 1 hour
  5. extractionthe reaction mixture was extracted with methylene chloride
  6. washAn organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled
  9. customThe residue was purified
  10. customfurther recrystallized by a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-edd291e47ccb40c19a516fbc826b49a9
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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