Hydrochloric Acid → HCID 69885803, compound

HRID 47721Notes

Reaction equation

HRID 47721 reaction equation
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:19]>C(OCC)C>[ClH:19].[C:13]1([CH2:12][C@@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86584424N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(phenylmethyl)ethyl]thiourea

Product 1

HCID 69885803HCID 69885803, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

The process is performed as in Example 2, starting with 2 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(phenylmethyl)ethyl]thiourea and 20 cm3 of aqueous 6N hydrochloric acid. The reaction lasts 1 h 30 min. After cooling the reaction mass to a temperature in the region of 0° C., the solution is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. Crystallization of the oil obtained is initiated by addition of diethyl ether. The resulting precipitate is spin-filtered, washed with twice 10 cm3 of diethyl ether and then dried under reduced pressure (10 Pa) at a temperature in the region of 60° C. The product is purified by taking it up in 100 cm3 of dichloromethane with stirring for 30 minutes. After filtration of the suspension, the filter cake is washed with twice 10 cm3 of dichloromethane and is then dried under the same conditions as above. 1.1 g of (+)-(4R)-4-phenylmethyl-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride are obtained in the form of a white solid melting at 168° C. (αD20=+8.7±0.3 at a concentration of 1% in methanol).

Workup

  1. concentrationthe solution is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  2. customCrystallization of the oil
  3. customobtained
  4. filtrationThe resulting precipitate is spin-filtered
  5. washwashed with twice 10 cm3 of diethyl ether
  6. customdried under reduced pressure (10 Pa) at a temperature in the region of 60° C
  7. customThe product is purified
  8. filtrationAfter filtration of the suspension
  9. washthe filter cake is washed with twice 10 cm3 of dichloromethane
  10. customis then dried under the same conditions as above

Sources & evidence

ORD record
ord-ecfa3f5d9ea64a7995ba15f3cdcd675d
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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