Water → 7-chloro-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbonitrile

HRID 704170Notes

Reaction equation

HRID 704170 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]([CH3:21])[CH2:17][NH:18][CH2:19][CH3:20])[C:11]1[CH:10]=[C:9]([C:22]#[N:23])[CH:8]=[CH:7][C:6]=1[S:5]2.I[CH2:25][CH3:26].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]([CH3:21])[CH2:17][N:18]([CH2:25][CH3:26])[CH2:19][CH3:20])[C:11]1[CH:10]=[C:9]([C:22]#[N:23])[CH:8]=[CH:7][C:6]=1[S:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 159252517-chloro-10-[(2RS)-1-ethylamino-2-propyl]-2-phenothiazinecarbonitrile

Product 1

HCID 159252497-chloro-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-chloro-10-[(2RS)-1-ethylamino-2-propyl]-2-phenothiazinecarbonitrile (5 g), iodethane (2.2 cc) and sodium carbonate (2 g) in dimethylformamide (50 cc) is charged, and the mixture is brought for 9 hours to 160° C. After cooling, the reaction mixture is poured into a mixture of distilled water (500 cc) and ethyl acetate (500 cc). The organic phase is separated after settling has taken place, washed with distilled water (4×300 cc), dried over magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give 7-chloro-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbonitrile (5 g).

Workup

  1. additionis charged
  2. temperatureAfter cooling
  3. customThe organic phase is separated after settling
  4. washwashed with distilled water (4×300 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-faad7f864ea5457a8bd1129096ea8294
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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