Iodoethane → HCID 20542216, compound

HRID 2286204Notes

Reaction equation

HRID 2286204 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[NH:4][CH:3]1[C:14]([NH:16][C:17]1[C:22](=[O:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[O:19][CH:18]=1)=[O:15].[H-].[Na+].[CH2:30](I)[CH3:31]>CN(C)C=O>[CH2:30]([N:4]1[CH:3]([C:14]([NH:16][C:17]2[C:22](=[O:23])[C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[O:19][CH:18]=2)=[O:15])[C:2](=[O:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5]1(=[O:13])=[O:12])[CH3:31]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13290587HCID 13290587, compound

Product 1

HCID 20542216HCID 20542216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,0 g of 3,4-dihydro-4-oxo-N-(4-oxo-4H-1-benzopyran-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and 0,68 g of a sodium hydride suspension (50% in petroleum) are dissolved, with rigorous stirring, in 100 ml of dimethylformamide of 4°. 2,5 g of ethyl iodide are added and allowed to react for 2 hours. The reaction mixture is concentrated to one-third of its original volume, and ethanol is slowly added until crystals begin to precipitate. After some standing at room temperature, the crystals are filtered off, washed with ice-cold ethanol and recrystallised from ethanol/chloroform. After filtration and drying, 2-ethyl-3,4-dihydro-4-oxo-N-(4-oxo-4H-1-benzopyran-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, of m.p. 235°-237°, is obtained.

Workup

  1. customto react for 2 hours
  2. concentrationThe reaction mixture is concentrated to one-third of its original volume, and ethanol
  3. additionis slowly added until crystals
  4. customto precipitate
  5. filtrationAfter some standing at room temperature, the crystals are filtered off
  6. washwashed with ice-cold ethanol
  7. customrecrystallised from ethanol/chloroform
  8. filtrationAfter filtration
  9. customdrying

Sources & evidence

ORD record
ord-094cf311add841cebef9d57918ed1800
Source dataset
uspto-grants-1982_04
Patent number
US04327091

Reaction notes

Loading…