Hydrochloric Acid → HCID 69885130, compound

HRID 47752Notes

Reaction equation

HRID 47752 reaction equation
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:19]>CC(O)C>[ClH:19].[ClH:19].[N:16]1[CH:17]=[CH:18][C:13]([CH2:12][C@@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86584437HCID 86584437, compound

Product 1

HCID 69885130HCID 69885130, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The process is performed under the conditions of Example 1 starting with 0.46 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(4-pyridylmethyl)ethyl]thiourea which is heated in 5 cm3 of aqueous 5 N hydrochloric acid for 16 hours at a temperature in the region of 100° C. After concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., an oil is obtained which is taken up in 3 cm3 of 2-propanol. The resulting crystalline precipitate is spin-filtered, washed with 2-propanol and air-dried. 0.1 g of (+)-(4R)-4-(4-pyridylmethyl)-4,5-dihydro-1,3-thiazol-2-ylamine dihydrochloride is obtained in the form of an orange-colored solid melting at 150° C. (αD20=+38.3±0.9 at a concentration of 0.5% in MeOH).

Workup

  1. customAfter concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., an oil is obtained which
  2. filtrationThe resulting crystalline precipitate is spin-filtered
  3. washwashed with 2-propanol
  4. customair-dried

Sources & evidence

ORD record
ord-71d0fa3915d749ee9296c1aa94937fa6
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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