Hydrochloric Acid → (4RS)-4-(5-thiazolylmethyl)-4,5-dihydro-thiazol-2-ylamine dihydrochloride

HRID 47756Notes

Reaction equation

HRID 47756 reaction equation
C([NH:5][C:6]([NH:8][CH:9]([CH2:16]O)[CH2:10][C:11]1[S:15][CH:14]=[N:13][CH:12]=1)=[S:7])(C)(C)C.[ClH:18]>>[ClH:18].[ClH:18].[S:15]1[C:11]([CH2:10][CH:9]2[CH2:16][S:7][C:6]([NH2:5])=[N:8]2)=[CH:12][N:13]=[CH:14]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22747917HCID 22747917, compound

Product 1

HCID 22747851(4RS)-4-(5-thiazolylmethyl)-4,5-dihydro-thiazol-2-ylamine dihydrochloride

Conditions

Temperature
110 °C

Procedure

a solution of 0.56 g of N-(tert-butyl)-N′-[(1RS)-1-hydroxymethyl-2-(5-thiazolyl)ethyl]thiourea in 5.5 cm3 of 6N hydrochloric acid is heated at a temperature in the region of 110° C. for 3 hours. The reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C., taken up in 4 cm3 of ethanol and 6 cm3 of diethyl ether and evaporated under the same conditions as above. The residue is taken up in 6 cm3 of ethanol and filtered, and the solid is dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C. and then dissolved in 5.5 cm3 of 6N hydrochloric acid solution and refluxed at a temperature in the region of 110° C. for 9 hours. The reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. and dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C., to give 0.54 g of (4RS)-4-(5-thiazolylmethyl)-4,5-dihydro-thiazol-2-ylamine dihydrochloride in the form of a pasty solid [1HNMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): from 3.20 to 3.40 (mt: 3H); from 3.60 to 3.80 (mt: 1H); 4.57 (mt: 1H); 7.85 (s, 1H); 9.10 (s: 1H); 9.26 (unresolved complex: 1H); 9.66 (unresolved complex: 1H); 10.13 (broad s: 1H].

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 60° C.
  2. custom6 cm3 of diethyl ether and evaporated under the same conditions as above
  3. filtrationfiltered
  4. customthe solid is dried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C.
  5. dissolutiondissolved in 5.5 cm3 of 6N hydrochloric acid solution
  6. concentrationThe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C.
  7. customdried in a desiccator under reduced pressure (0.1 kPa) at a temperature in the region of 40° C.

Sources & evidence

ORD record
ord-6a72a1c0207d405ba4abd95c7e99b79d
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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