Iodoethane → HCID 12223716, compound

HRID 1658062Notes

Reaction equation

HRID 1658062 reaction equation
[H-].[Na+].[F:3][C:4]([F:25])([F:24])[C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9]4=[C:10]([C:19](=[O:23])[NH:20][C:21](=[O:22])[N:8]4[C:7]=2[CH:6]=1)[CH:11]=[CH:12][CH:13]=3.[CH2:26](I)[CH3:27]>CN(C)C=O>[CH2:26]([N:20]1[C:19](=[O:23])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[S:15][C:16]4[CH:17]=[CH:18][C:5]([C:4]([F:24])([F:3])[F:25])=[CH:6][C:7]=4[N:8]([C:9]=23)[C:21]1=[O:22])[CH3:27]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1222371510-Trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine-1,3-(2H)-dione

Product 1

HCID 12223716HCID 12223716, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

57% Sodium hydride in mineral oil (4.2 g., 0.100 mol.) was added to a stirred solution of 28.0 g. (0.0834 mol.) of 10-trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine -1,3(2H)-dione in 220 ml. of dry dimethylformamide. The mixture was stirred for 1 hour at 25°, then 16.8 g. (8.6 ml., 0.108 mol.) of ethyl iodide was added. The resulting greenish yellow, turbid mixture was stirred for 4.5 hours at 25°, then filtered to give a clear yellow solution. The filtrate was evaporated to dryness under reduced pressure and the residue was triturated with petroleum ether to remove the mineral oil. The crude solid product was precipitated from a methanol-water mixture to give the title compound, m.p. 150°-152° (ethanol).

Workup

  1. stirringThe resulting greenish yellow, turbid mixture was stirred for 4.5 hours at 25°
  2. filtrationfiltered
  3. customto give a clear yellow solution
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. customthe residue was triturated with petroleum ether
  6. customto remove the mineral oil
  7. customThe crude solid product was precipitated from a methanol-water mixture

Sources & evidence

ORD record
ord-4f4a0ce4a33547c2b1a2ea10f675a0d3
Source dataset
uspto-grants-1976_06
Patent number
US03962438

Reaction notes

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