Ethylamine → HCID 14536548, compound

HRID 704197Notes

Reaction equation

HRID 704197 reaction equation
[CH2:1]([NH2:3])[CH3:2].CS(O[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26]#[N:27])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])(=O)=O>C1(C)C=CC=CC=1>[CH2:1]([NH:3][CH2:11][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26]#[N:27])[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14536548HCID 14536548, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethylamine (18.75 cc) is added to a solution of 2-(2-cyano-10-phenothiazinyl)-1-propyl methanesulphonate, D series (10 g) in toluene (100 cc), and this mixture is brought to a temperature in the region of 105° C. for 24 hours. After cooling, the reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with ethyl ether (250 cc) and extracted successively with N-aqueous hydrochloric solution (2×100 cc). The combined aqueous phases are alkalinized with caustic soda (d=1.33) to pH 13 and extracted with ethyl ether (2×200 cc). The combined organic phases are washed successively with distilled water (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. 10-(1-Ethylamino-2-propyl)-2-phenothiazinecarbonitrile, D series (5 g) is thereby obtained in the form of an orange oil. This product is dissolved at a temperature in the region of 60° C. in ethanol (17 cc), and this solution is poured into a solution of fumaric acid (1.9 g) in ethanol (17 cc) at the same temperature, crystallization is then primed and the mixture is left for 16 hours at a temperature in the region of 20° C. The solid is drained, washed with ethanol (2×2 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. 10-(1-Ethylamino-2-propyl)-2-phenothiazinecarbonitrile acid fumarate, D series (4 g) is thereby obtained in the form of a yellow solid, m.p. 208° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. extractionextracted successively with N-aqueous hydrochloric solution (2×100 cc)
  4. extractionextracted with ethyl ether (2×200 cc)
  5. washThe combined organic phases are washed successively with distilled water (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

Sources & evidence

ORD record
ord-7403fa4abcf34511a59badd184a30945
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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