Hydrochloric Acid → HCID 70548735, compound

HRID 1902553Notes

Reaction equation

HRID 1902553 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][C:9]1[S:13][C:12]([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)=[N:11][CH:10]=1)=[O:7])C.[ClH:28]>C(O)C>[ClH:28].[C:6]([CH2:8][C:9]1[S:13][C:12]([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)=[N:11][CH:10]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54242313HCID 54242313, compound

Product 1

HCID 70548735HCID 70548735, 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-[(5-ethoxycarbonylmethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (7.9 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; 10 cc). The resulting precipitate is filtered off and washed with water (3×50 cc) and then with ethanol (50 cc) and diethyl ether (20 cc). The product is recrystallised by dissolving it in dimethylformamide (15 cc) at 70° C., adding ethanol (80 cc) and cooling to 0° C. The resulting crystals are filtered off, washed with ethanol (50 cc) and then with diethyl ether (20 cc) and dried at 50° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(5-carboxymethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline hydrochloride (6.8 g), melting at about 240° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for two hours
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water (3×50 cc)
  5. customThe product is recrystallised
  6. dissolutionby dissolving it in dimethylformamide (15 cc) at 70° C.
  7. additionadding ethanol (80 cc)
  8. temperaturecooling to 0° C
  9. filtrationThe resulting crystals are filtered off
  10. washwashed with ethanol (50 cc)
  11. dry with materialwith diethyl ether (20 cc) and dried at 50° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-73951a9acbc24e6cbd528a702c6ffbcf
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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