Hydrochloric Acid → HCID 70548603, compound

HRID 1902560Notes

Reaction equation

HRID 1902560 reaction equation
[OH-].[Na+].C[O:4][C:5]([CH2:7][C:8]1[S:12][C:11]([N:13]=[C:14]2[N:18]3[CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[CH2:26][C@H:17]3[CH2:16][S:15]2)=[N:10][C:9]=1[CH3:27])=[O:6].[ClH:28]>C(O)C>[ClH:28].[C:5]([CH2:7][C:8]1[S:12][C:11]([N:13]=[C:14]2[N:18]3[CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[CH2:26][C@H:17]3[CH2:16][S:15]2)=[N:10][C:9]=1[CH3:27])([OH:6])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53873336HCID 53873336, compound

Product 1

HCID 70548603HCID 70548603, 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-methoxycarbonylmethyl-4-methylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (8.1 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, washed with water (5×25 cc), ethanol (3×15 cc) and diethyl ether (2×25 cc) and recrystallised by dissolving it in dimethylformamide (80 cc) at 150° C. and cooling to 0° C. The resulting crystals are filtered off, washed with dimethylformamide (10 cc), ethanol (4×15 cc) and diethyl ether (3×15 cc) and dried at 45° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(5-carboxymethyl-4-methylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline hydrochloride (4.8 g), as a white solid melting at about 250° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for two hours
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water (5×25 cc), ethanol (3×15 cc) and diethyl ether (2×25 cc)
  5. customrecrystallised
  6. dissolutionby dissolving it in dimethylformamide (80 cc) at 150° C.
  7. temperaturecooling to 0° C
  8. filtrationThe resulting crystals are filtered off
  9. washwashed with dimethylformamide (10 cc), ethanol (4×15 cc) and diethyl ether (3×15 cc)
  10. customdried at 45° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-aa2e294bc0ef44a998fe065e5f041fba
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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