Hydrochloric Acid → (+)-(4R)-4-(3-nitrobenzyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride

HRID 1280600Notes

Reaction equation

HRID 1280600 reaction equation
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:22]>>[ClH:22].[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C@@H:9]1[CH2:10][S:7][C:6]([NH2:5])=[N:8]1)([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86584418N-(tert-butyl)-N'-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea

Product 1

HCID 69885146(+)-(4R)-4-(3-nitrobenzyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride

Conditions

Temperature
0 °C

Procedure

1.1 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea in 12 cm3 of 6N hydrochloric acid are heated for 5 hours at a temperature in the region of 100° C. The reaction medium is then cooled to a temperature in the region of 0° C.; a white precipitate forms, which is filtered off on a sinter funnel and then washed with 3 times 20 cm3 of diethyl ether. The filter cake is then dried in a desiccator under vacuum. 0.68 g of (+)-(4R)-4-(3-nitrobenzyl)-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride is obtained in the form of beige-colored crystals melting at 232° C. [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 3.15 (limiting AB: 2H); from 3.25 to 3.45 (mt: 1H); 3.63 (dd, J=13 and 8 Hz: 1H); 4.62 (mt: 1H); 7.68 (t, J=8 Hz: 1H); 7.81 (broad d, J=8 Hz: 1H); 8.18 (broad d, J=8 Hz: 1H); 8.24 (broad s: 1H); from 9.00 to 10.40 (unres. (a20 mult.: 3H); (αD20=+18.8±0.6 at a concentration of 0.5% in methanol)].

Workup

  1. filtrationa white precipitate forms, which is filtered off on a sinter funnel
  2. washwashed with 3 times 20 cm3 of diethyl ether
  3. customThe filter cake is then dried in a desiccator under vacuum

Sources & evidence

ORD record
ord-a6e73c4af919441b91b2daea6b569b4b
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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