Water → HCID 21410883, compound

HRID 2072180Notes

Reaction equation

HRID 2072180 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:12][C:13]([NH2:15])=[S:14].O>C(O)C.Cl>[ClH:1].[NH2:12][CH:13]1[N:15]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:3]=[CH:2][S:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 702953-ChloropropiophenoneHCID 2723790Thiourea

Product 1

HCID 21410883HCID 21410883, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

20.3 g (0.1 mol) of β-chloroethyl-phenyl ketone together with 7.6 g (0.1 mol) of thiourea in 100 ml of ethanol in which 0.5% by weight of hydrogen chloride is dissolved, are heated to the boil (for about 3 to 4 hours) until the starting compounds can no longer be detected in a sample by thin-layer chromatography. Thereafter ethanol is azeotropically distilled off whilst toluene is continuously added in the same amount as ethanol distils off and the resulting toluene reaction mixture is boiled for a further 1/2 hour on the water separator. 23 g (about 88% of the theory) of crude 2-amino-4-phenyl-1,3-thiazine hydrochloride (m.p. 204° C.) separate out as faintly yellow-coloured crystals and are filtered off. By recrystallizing from ethanol, pure 2-amino-4-phenyl-1,3-thiazine-hydrochloride is obtained with a melting point of 210° C.

Workup

  1. temperatureare heated to the boil (for about 3 to 4 hours) until the starting compounds
  2. distillationThereafter ethanol is azeotropically distilled off whilst toluene
  3. additionis continuously added in the same amount as ethanol
  4. customdistils off
  5. customthe resulting toluene reaction mixture
  6. custom23 g (about 88% of the theory) of crude 2-amino-4-phenyl-1,3-thiazine hydrochloride (m.p. 204° C.) separate out as faintly yellow-coloured crystals
  7. filtrationare filtered off
  8. customBy recrystallizing from ethanol

Sources & evidence

ORD record
ord-3020044d550c42218e97fdccf425b43c
Source dataset
uspto-grants-1977_09
Patent number
US04049807

Reaction notes

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