Hydrochloric Acid → (+)-(4R)-4-(4-thiazolylmethyl)-4,5-dihydro-2-thiazolylamine dihydrochloride
Reaction equation
C([NH:5][C:6]([NH:8][C@@H:9]([CH2:16]O)[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[S:7])(C)(C)C.[ClH:18]>>[ClH:18].[ClH:18].[S:14]1[CH:15]=[C:11]([CH2:10][C@@H:9]2[CH2:16][S:7][C:6]([NH2:5])=[N:8]2)[N:12]=[CH:13]1Participants
Procedure
A solution of 1.75 g of N-(tert-butyl)-N′-[(1R)-1-hydroxymethyl-2-(4-thiazolyl)ethyl]thiourea in 20 cm3 of 6N hydrochloric acid is heated at a temperature in the region of 110° C. for 20 hours. The reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C., taken up in 5 cm3 of ethanol and then concentrated under the same conditions as above. The residue is taken up in 5 cm3 of ethanol and the product is then filtered off and dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C. 0.54 g of (+)-(4R)-4-(4-thiazolylmethyl)-4,5-dihydro-2-thiazolylamine dihydrochloride is obtained in the form of a cream-coloured solid melting at 195° C. [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 3.67 (mt: 2H); 3.41 (dd, J=11.5 and 5.5 Hz: 1H); 3.68 (dd, J=11.5 and 8 Hz: 1H); 4.63 (mt: 1H); 7.59 (d, J=2 Hz: 1H); 9.14 (d, J=2 Hz: 1H); 9.18 (unresolved complex: 1H); 9.66 (unresolved complex: 1H); 10.04 (broad s: 1H); (αD20=+24.2+/−0.8 at a concentration of 0.5% in methanol)].
Workup
- concentrationThe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C.
- concentrationconcentrated under the same conditions as above
- filtrationthe product is then filtered off
- customdried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C
Sources & evidence
- ORD record
- ord-cb492bbcd12d45c6adb5fbf812472c0f
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451821B1
Reaction notes
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