2-Bromoethanol → HCID 15925269, compound

HRID 704179Notes

Reaction equation

HRID 704179 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([N:6]1[C:19]2[CH:18]=[C:17]([C:20]#[N:21])[CH:16]=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5].C(=O)([O-])O.[Na+].Br[CH2:28][CH2:29][OH:30]>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH:4]([N:6]1[C:19]2[CH:18]=[C:17]([C:20]#[N:21])[CH:16]=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5])[CH2:28][CH2:29][OH:30]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 15925256HCID 15925256, compound

Product 1

HCID 15925269HCID 15925269, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 10-[(2RS)-1-methylamino-2-propyl]-2-phenothiazinecarbonitrile (3.7 g), sodium hydrogen carbonate (1.6 g) and 2-bromoethanol (0.9 cc) in dimethylformamide (60 c ) is heated under reflux for 6 hours 15 minutes. After cooling, the mixture is concentrated to dryness under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. The residue is taken up with ethyl acetate (100 cc), washed successively with distilled water (2×50 cc) and with saturated aqueous sodium chloride solution (50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (4.4 g) is purified by chromatography on a column (height: 35 cm; diameter: 2.6 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (70:30 by volume) (1.25 liters) of ethyl acetate and cyclohexane and collecting 50-cc fractions. The combined fractions 9 to 22 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (3.1 g) is thereby obtained in the form of a yellow oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours 15 minutes
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated to dryness under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C
  5. washwashed successively with distilled water (2×50 cc) and with saturated aqueous sodium chloride solution (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. customThe residual orange oil (4.4 g) is purified by chromatography on a column (height: 35 cm; diameter: 2.6 cm) of silica gel (0.2-0.063 mm)
  10. washeluting with a mixture (70:30 by volume) (1.25 liters) of ethyl acetate and cyclohexane
  11. customcollecting 50-cc fractions
  12. concentrationThe combined fractions 9 to 22 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-ccd8060f39224ac2bf7c5fe0c3aed08a
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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