Hydrochloric Acid → HCID 12051226, compound

HRID 985547Notes

Reaction equation

HRID 985547 reaction equation
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][CH2:13][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[CH2:10]O)=[S:7])(C)(C)C.Cl>C(O)C>[S:16]1[CH:17]=[CH:18][C:14]([CH2:13][CH2:12][C@@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)=[CH:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9965687HCID 9965687, compound

Product 1

HCID 12051226HCID 12051226, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.72 g of N-(tert-butyl)-N′-[(1R)-2-hydroxy-1-(2-thien-3-yl-ethyl)ethyl]-thiourea in 20 mL of aqueous solution of 5N hydrochloric acid is heated under magnetic stirring at a temperature of about 100° C. for 18 hours. The reaction medium is then evaporated under reduced pressure (2 kPa) at a temperature of about 40° C. and the residue obtained is taken up in 20 mL of ethanol and concentrated again according to the conditions described above. The evaporating residue is taken up in 5 mL of ethanol, filtered, washed with 2 times 2 mL of ethanol and with 2 times 5 mL of ethyl ether. The product is dried in an oven under vacuum (10 Pa) at a temperature of about 20° C. About 0.28 g of (4R)-4-(2-thien-3-ylethyl)-4,5-dihydro-1,3-thiazol-2-ylamine, chlorhydrateare are obtained in the form of a colored-beige solid melting at 150° C. [1H NMR spectrum (300 MHz, (CD3)2SO d6, δ in ppm): from 1.85 to 2.10 (mt, 2H); 2.70 (mt, 2H); from 3.30 to 3.45 (mt, 1H); 3.69 (dd, J=11 and 7.5 Hz, 1H); 4.21 (mt, 1H); 7.05 (dd, J=5 and 1.5 Hz, 1H); 7.26 (mt, 1H); 7.50 (dd, J=5 and 3 Hz, 1H); 9.10 (mf, 1H); 9.61 (mf, 1H); 10.27 (s large, 1H)].

Workup

  1. temperatureis heated
  2. customThe reaction medium is then evaporated under reduced pressure (2 kPa) at a temperature of about 40° C.
  3. customthe residue obtained
  4. concentrationconcentrated again
  5. filtrationfiltered
  6. washwashed with 2 times 2 mL of ethanol and with 2 times 5 mL of ethyl ether
  7. customThe product is dried in an oven under vacuum (10 Pa) at a temperature of about 20° C

Sources & evidence

ORD record
ord-e22b06fae56e461fad1b9f21dd227054
Source dataset
uspto-grants-2005_03
Patent number
US06872740B2

Reaction notes

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