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Iodoethane → 10-(1-Diethylamino-2-propyl)-2-phenothiazinecarbonitrile

HRID 728721
Notes
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Reaction equation

HRID 728721 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].I[CH2:30][CH3:31]>CN(C)C=O>[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 14536548HCID 14536548, compound

Product 1

HCID 1453650710-(1-Diethylamino-2-propyl)-2-phenothiazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 10-(1-ethylamino-2-propyl)-2-phenothiazinecarbonitrile acid fumarate, D series (4 g), sodium carbonate (1.32 g) and iodoethane (1 cc) in dimethylformamide (50 cc) is heated to a temperature in the region of 150° C. for 6 hours. After being cooled, the reaction mixture is concentrated to dryness (30 mm Hg; 4 kPa) at 50° C. and the residue is taken up with ethyl acetate (100 cc) and washed successively with distilled water (50 cc) and with saturated aqueous sodium chloride solution (50 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-(1-Diethylamino-2-propyl)-2-phenothiazinecarbonitrile, D series (3.4 g) is thereby obtained in the form of a yellow oil.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe reaction mixture is concentrated to dryness (30 mm Hg; 4 kPa) at 50° C.
  3. washwashed successively with distilled water (50 cc) and with saturated aqueous sodium chloride solution (50 cc)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-fcdade080e82490688b0c5ba6d8f204a
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05049669

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes