Hydrochloric Acid → HCID 70548697, compound

HRID 1902558Notes

Reaction equation

HRID 1902558 reaction equation
[OH-].[Na+].C[O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]=[C:17]2[N:21]3[CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[CH2:29][C@H:20]3[CH2:19][S:18]2)[S:14][CH:15]=1)=[O:6].[ClH:30].C(OCC)C>C(O)C>[ClH:30].[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]=[C:17]2[N:21]3[CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[CH2:29][C@H:20]3[CH2:19][S:18]2)[S:14][CH:15]=1)([OH:6])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53976911HCID 53976911, compound

Product 1

HCID 70548697HCID 70548697, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

5 N Aqueous sodium hydroxide (20 cc) is added to a solution of (S)-3-{[4-(4-methoxycarbonylbutyl)-thiazol-2-yl]imino}-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (7.4 g) in ethanol (60 cc). The mixture is heated under reflux for 2 hours. After cooling to 20° C., it is acidified by adding 12 N hydrochloric acid (d=1.19; 10 cc). Diethyl ether (30 cc) is added and the mixture is cooled to 0° C. The resulting precipitate is filtered off, washed with water (4×15 cc), ethanol (2×10 cc) and diethyl ether (2×30 cc) and crystallised by dissolving it in boiling propan-2-ol (200 cc) and cooling to 0° C. The resulting crystals are filtered off, washed with propan-2-ol (20 cc) and diethyl ether (50 cc) and dried at 45° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-{[4-(4-carboxybutyl)thiazol-2-yl]imino}-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline hydrochloride (4.9 g), m.p.=214° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture is cooled to 0° C
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with water (4×15 cc), ethanol (2×10 cc) and diethyl ether (2×30 cc)
  6. customcrystallised
  7. dissolutionby dissolving it
  8. temperaturecooling to 0° C
  9. filtrationThe resulting crystals are filtered off
  10. washwashed with propan-2-ol (20 cc) and diethyl ether (50 cc)
  11. customdried at 45° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-7fd3fe62dee54cfa95c0870d213dac0f
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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