Hydrochloric Acid → HCID 23655017, compound

HRID 556110Notes

Reaction equation

HRID 556110 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[N:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:27]>C(OCC)(=O)C>[ClH:27].[ClH:27].[ClH:27].[CH2:1]([C:8]1[S:12][C:11]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[N:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23655018HCID 23655018, compound

Product 1

HCID 23655017HCID 23655017, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.4 g (1.09 mmol) 1-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-piperazine prepared in Example 71 was dissolved in 20 ml ethyl acetate, cooled in ice-bath, added a 2 mol/L solution of hydrochloride in ethyl acetate under stirring, and a yellow solid was produced, which was filtered in vacuo, and washed with ethyl acetate to give 3.4 g product as a yellow solid in a yield of 77.3%, mp: 111-112 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 3.19 (4H, m, 2×CH2), 3.62 (4H, m, 2×CH2), 3.79 (3H, s, OCH3), 4.12 (2H, s, CH2), 5.58 (2H, br, exchangeable, 2×NH), 6.98 (2H, d, J=8.80 Hz, ArH), 7.18˜7.32 (5H, m, ArH), 7.52 (2H, d, J=8.80 Hz, ArH), 9.34 (2H, br, exchangeable, 2×NH); EI-MS m/e (%): 365.0 (M−3, 81), 323.0 (26), 309.0 (100), 295.9 (51); HREI-MS Calcd. for C21H23N3OS: 365.1562. found: 365.1564.

Workup

  1. temperaturecooled in ice-bath
  2. customa yellow solid was produced
  3. filtrationwhich was filtered in vacuo
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-136badad3895416c975754b322ee8d92
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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