Iodoethane → N-ethyl-N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

HRID 36078Notes

Reaction equation

HRID 36078 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8]C(C)(C)[CH:6]=1)=[O:4].[CH2:20](I)[CH3:21].[H-].O1CC[CH2:26][CH2:25]1.Cl[CH2:30]Cl>>[CH2:25]([N:2]([CH3:1])[C:3]([C:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:20]([CH3:21])([CH3:30])[CH:6]=1)=[O:4])[CH3:26]

Participants

6

Reactant 5

HCID 6340IodoethaneHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 166653HydrideHCID 15234733N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

Product 1

HCID 15234736N-ethyl-N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

Procedure

A mixture of 0.53 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide, 1.60 g of ethyl iodide, 0.09 g of sodlum hydride, and 10 ml of tetrahydrofuran was heated at reflux for 30 minutes. Dichloromethane was added to the reaction mixture, and any insoluble matter was removed by filtration. The filtrate was recrystallized from a mixture of diethyl ether and n-hexane to obtain 0.45 g of N-ethyl-N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. customany insoluble matter was removed by filtration
  4. customThe filtrate was recrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-045e968bcdcc4bc08bd08d84a4d9ffb7
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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