Hydrochloric Acid → Benzenamine, 3-(2,3,5,6-tetrahydroimidazo(2,1-b)thiazol-6-yl)-, dihydrochloride, (+-)-

HRID 597574Notes

Reaction equation

HRID 597574 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]2[CH2:6][CH:7]([C:9]3[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=3)[NH:12]C(=O)C)[N:8]=[C:2]12.[ClH:19]>CO.CC(O)C>[ClH:19].[ClH:19].[NH2:12][C:11]1[CH:10]=[C:9]([CH:7]2[CH2:6][N:3]3[C:2]([S:1][CH2:5][CH2:4]3)=[N:8]2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 128505123'-(2,3,5,6-Tetrahydroimidazo[2,1-b]thiazol-6-yl)acetanilide

Product 1

HCID 3038668Benzenamine, 3-(2,3,5,6-tetrahydroimidazo(2,1-b)thiazol-6-yl)-, dihydrochloride, (+-)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1.00 g. (0.0038 mole) of 3'-(2,3,5,6-tetrahydroimidazo[2,1-b]thiazol-6-yl)acetanilide (Example 8) in 17 ml. of 6N hydrochloric acid is heated at reflux for 2.5 hours and then allowed to stand overnight at room temperature. The solution is concentrated at reduced pressure, made basic with concentrated aqueous sodium hydroxide while cooling and then extracted with 3 portions of chloroform. The combined organic layers are washed with brine, dried (sodium sulfate) and evaporated to give 0.84 g. of an oil, i.e., m-aminotetramisole free base. The oil is dissolved in hot methanol and strongly acidified with hydrogen chloride in 2-propanol. Evaporation of the solution and crystallization of the residue from 2-propanol gives 0.91 g. (81%) of cream colored solid, melting point 198°-201° C., dec.

Workup

  1. temperatureat reflux for 2.5 hours
  2. concentrationThe solution is concentrated at reduced pressure
  3. temperaturewhile cooling
  4. extractionextracted with 3 portions of chloroform
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. customto give 0.84 g
  9. customEvaporation of the solution and crystallization of the residue from 2-propanol
  10. customgives 0.91 g

Sources & evidence

ORD record
ord-a94c9eae0dbe45aaab3357ae7188520f
Source dataset
uspto-grants-1977_03
Patent number
US04014892

Reaction notes

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