Iodoethane → HCID 13784682, compound

HRID 235633Notes

Reaction equation

HRID 235633 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]2[C:22](=[O:23])[NH:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[S:18]2)[CH2:11][CH2:10]1.[H-].[Na+].[CH2:30](I)[CH3:31]>CN(C)C=O>[CH2:30]([N:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][CH:17]([CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]2)[C:22]1=[O:23])[CH3:31]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13784676HCID 13784676, compound

Product 1

HCID 13784682HCID 13784682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 1.0 g of 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one, in 10 ml of dimethylformamide, was added 120 mg of 60% sodium hydride in oil at room temperature with stirring. The mixture was stirred for 10 minutes and 480 mg of ethyl iodide was added thereto. The whole mixture was stirred for further two hours, poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and concentrated. The residue was subjected to a column chromatography on silica-gel (50 g). From the eluate with hexane-ethyl acetate (2:1, v/v) was obtained 4-ethyl-2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one as an oily substance (0.60 g). This product was crystallized as the hydrochloride. The yield was 0.50 g (39%). Recrystallization from methanol-ether gave colorless prisms, m.p. 142°-144° C.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. stirringThe whole mixture was stirred for further two hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0727ab2a1a244625b3470e4860449a8d
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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