Methylamine → N-Methyl-[2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetamide

HRID 1200189Notes

Reaction equation

HRID 1200189 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=O)=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:22]([N:24](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN>ClCCl>[CH3:22][NH:24][C:19](=[O:21])[CH2:18][C:17]1[C:9]2[O:8][C:7]([C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=3)=[CH:12][C:11](=[O:13])[C:10]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 14650449HCID 14650449, compound

Product 1

HCID 14650457N-Methyl-[2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (568 mg) and triethylamine (0.34 ml) were added to dichloromethane (6 ml) and to the mixture was added dropwise diphenylphosphoryl azide (0.52 ml) with stirring at room temperature. After stirring for 30 minutes, 30% aqueous methylamine solution (5 ml) was added and stirring was continued for additional 2 hours. The solvent was distilled off under reduced pressure and n-hexane was added to the residue. Crystals deposited were filtered. The crude crystals were recrystallized from methanol to obtain the title compound as prisms, yield 380 mg (64%), m.p. 213°-214° C.

Workup

  1. stirringAfter stirring for 30 minutes
  2. stirringstirring
  3. distillationThe solvent was distilled off under reduced pressure and n-hexane
  4. additionwas added to the residue
  5. filtrationCrystals deposited were filtered
  6. customThe crude crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-d3bf68338ce34608b37aa22bb812ae78
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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