Hydrogen Bromide → 4-[4-[4-[(3-Butyltetrahydro-1,3-thiazin-2-ylidene)amino]phenyl]-1-piperazinyl]phenol

HRID 648491Notes

Reaction equation

HRID 648491 reaction equation
Br.S([O-])(O)=O.[Na+].[CH2:7]([N:11]([CH2:35][CH2:36][CH2:37]O)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)=[S:13])[CH2:8][CH2:9][CH3:10]>O>[CH2:7]([N:11]1[CH2:35][CH2:36][CH2:37][S:13][C:12]1=[N:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[CH2:23][CH2:22]2)=[CH:19][CH:20]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 13732393N-butyl-N-(3-hydroxypropyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thioureaHCID 23665763Sodium Bisulfite

Product 1

HCID 137323984-[4-[4-[(3-Butyltetrahydro-1,3-thiazin-2-ylidene)amino]phenyl]-1-piperazinyl]phenolYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 75 parts of a hydrobromic acid solution 48% in water was added a small amount of sodium hydrogen sulfite. Then there were added 1.7 parts of N-butyl-N-(3-hydroxypropyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea. The whole was stirred and refluxed for 3 hours. The reaction mixture was evaporated. The residue was dissolved in a mixture of methanol and water. The solution was neutralized with a sodium hydrogen carbonate solution. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 0.6 parts (38%) of 4-[4-[4-[(3-butyltetrahydro-1,3-thiazin-2-ylidene)amino]phenyl]-1-piperazinyl]phenol; mp. 143.0° C. (45).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture was evaporated
  3. dissolutionThe residue was dissolved in a mixture of methanol and water
  4. extractionThe product was extracted with dichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 2-propanol
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-05ca485da5f547d38a348ea8cf5c6d41
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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