Ethanol → ethyl (2RS)-2-(2-cyano-10-phenothiazinyl)propionate

HRID 1165787Notes

Reaction equation

HRID 1165787 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]#[N:16].[H-].[Na+].Cl[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(O)C>CN(C)C=O.O>[C:15]([C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:13]([CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]=2[CH:1]=1)#[N:16]

Participants

7

Reactant 4

HCID 702EthanolHCID 10807Ethyl 2-chloropropionateHCID 24758Sodium hydrideHCID 98841Phenothiazine-2-carbonitrile

Product 1

HCID 14502135ethyl (2RS)-2-(2-cyano-10-phenothiazinyl)propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-phenothiazinecarbonitrile (224.5 g) in dimethylformamide (1 liter) is poured into a suspension of sodium hydride (24 g) in dimethylformamide (1 liter) at a temperature of about 25° C., whilst stirring and in 2 hours 30 minutes, then the mixture is stirred for a further 1 hour 15 minutes until evolution of gas has ended. The fine suspension obtained is poured, with stirring and at a temperature of about 25° C., in 4 hours 30 minutes into a solution of ethyl 2-chloropropionate (255 cc) in dimethylformamide (1 liter) and stirring is continued for 16 hours. Ethanol (100 cc) is then poured into the reaction mixture then the whole is poured onto a mixture of ice (2 kg) in distilled water (4 liters): a gum precipitates and then crystallizes. The solid formed is centrifuged, washed successively with distilled water (6×500 cc) and petroleum ether (2×500 cc) and dried in air. Ethyl (2RS)-2-(2-cyano-10-phenothiazinyl)propionate (296.5 g) is thus obtained in the form of khaki-colored crystals which melt at 117°-8° C., used as such in the following stage.

Workup

  1. stirringthe mixture is stirred for a further 1 hour 15 minutes until evolution of gas
  2. customThe fine suspension obtained
  3. additionis poured
  4. stirringstirring
  5. waitis continued for 16 hours
  6. customa gum precipitates
  7. customcrystallizes
  8. customThe solid formed
  9. washwashed successively with distilled water (6×500 cc) and petroleum ether (2×500 cc)
  10. customdried in air

Sources & evidence

ORD record
ord-c4d2e202122b4f6fa1a6194827d4668e
Source dataset
uspto-grants-1990_03
Patent number
US04912105

Reaction notes

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