Hydrochloric Acid → HCID 70549861, compound

HRID 1902555Notes

Reaction equation

HRID 1902555 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][C:9]1[N:10]=[C:11]([N:14]=[C:15]2[N:19]3[CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[CH2:27][C@H:18]3[CH2:17][S:16]2)[S:12][CH:13]=1)=[O:7])C.[ClH:28]>C(O)C>[ClH:28].[C:6]([CH2:8][C:9]1[N:10]=[C:11]([N:14]=[C:15]2[N:19]3[CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[CH2:27][C@H:18]3[CH2:17][S:16]2)[S:12][CH:13]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54023959HCID 54023959, compound

Product 1

HCID 70549861HCID 70549861, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A 4 N aqueous solution of sodium hydroxide (30 cc) is added to a solution of (S)-3-[(4-ethoxycarbonylmethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinoline (10 g) in ethanol (60 cc). The mixture is heated under reflux for two hours. After cooling to 20° C., it is acidified by adding 12 N hydrochloric acid (d=1.19; 11 cc). The white precipitate which has formed is filtered off, washed with water and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). The resulting solid is crystallised by dissolving it in boiling ethanol (200 cc), cooling and filtering off the crystals formed; the product is then recrystallised by dissolving it in dimethylformamide (60 cc) at 100° C., adding ethanol (120 cc) and cooling to 0° C. The crystals are filtered off, washed with ethanol (20 cc) and then with diethyl ether (20 cc) and dried at 40° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(4-carboxymethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline hydrochloride (5.6 g), m.p.=206° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for two hours
  3. customThe white precipitate which has formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)
  7. customThe resulting solid is crystallised
  8. dissolutionby dissolving it
  9. temperaturecooling
  10. filtrationfiltering off the crystals
  11. customformed
  12. customthe product is then recrystallised
  13. dissolutionby dissolving it in dimethylformamide (60 cc) at 100° C.
  14. additionadding ethanol (120 cc)
  15. temperaturecooling to 0° C
  16. filtrationThe crystals are filtered off
  17. washwashed with ethanol (20 cc)
  18. dry with materialwith diethyl ether (20 cc) and dried at 40° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-2af10e12b82d4e188f38eae178e23026
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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