Ammonium Chloride → HCID 12992805, compound

HRID 1760265Notes

Reaction equation

HRID 1760265 reaction equation
[OH:1][C:2]1([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][O:26][CH2:27]Cl.[NH4+].[Cl-]>ClCCl>[CH3:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][O:26][CH2:27][O:1][C:2]1([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 12992811HCID 12992811, compound

Product 1

HCID 12992805HCID 12992805, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the alcohol 2-[(1-Hydroxy)cyclohexyl]thiazole from Step 1 (5.8 g, 32 mmol) and Hunig's base (14 mL, 67 mmol) in dichloromethane (100 mL) at 0° C. was added 2-(trimethylsilyl)ethoxymethyl chloride (6.5 mL, 36.7 mmol). The resulting solution was stirred at 0° C. for 15 min, was heated at reflux temperature for 15 h and then cooled to room temperature. Sat. aq. NH4Cl was added and the resulting mixture was extracted with dichloromethane (3×). The combined organics were washed with water, brine, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/ethyl acetate 7:3) provided 2-{1-[(2-Trimethylsilylethoxy)methoxy]cyclohexyl}thiazole (8 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 15 h
  3. temperaturecooled to room temperature
  4. extractionthe resulting mixture was extracted with dichloromethane (3×)
  5. washThe combined organics were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b49c1be2a69541f0b50ed91a5c3b9c02
Source dataset
uspto-grants-2005_01
Patent number
US06841564B2

Reaction notes

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