2-Bromoethanol → 2-(2-Hydroxyethyl)-10-trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine-1,3(2H)-dione

HRID 1658063Notes

Reaction equation

HRID 1658063 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.Br[CH2:27][CH2:28][OH:29]>CN(C)C=O>[OH:29][CH2:28][CH2:27][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]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 1222371510-Trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine-1,3-(2H)-dione

Product 1

HCID 122237172-(2-Hydroxyethyl)-10-trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

57% Sodium hydride in mineral oil (8.4 g., 0.200 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 54.0 g. (0.432 mol.) of 2-bromoethanol was added. The resulting mixture was stirred for 4.5 hours at 25°, then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed on silica gel with chloroform and 90% chloroform-methanol as eluants to give the title compound, m.p. 90°-93° (methanol).

Workup

  1. stirringThe resulting mixture was stirred for 4.5 hours at 25°
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed on silica gel with chloroform and 90% chloroform-methanol as eluants

Sources & evidence

ORD record
ord-abfdd56c44524c78aee8c0fd7e702b5a
Source dataset
uspto-grants-1976_06
Patent number
US03962438

Reaction notes

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