Ammonium Chloride → 1-(2,4-Dimethyl-5-thiazolyl)-1-(4-methyl-2-thiazolyl)ethanol

HRID 1377560Notes

Reaction equation

HRID 1377560 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[C:9]([Si](C)(C)C)[S:10][CH:11]=1.[C:16]([C:19]1[S:23][C:22]([CH3:24])=[N:21][C:20]=1[CH3:25])(=[O:18])[CH3:17].[Cl-].[NH4+]>O1CCCC1>[CH3:24][C:22]1[S:23][C:19]([C:16]([C:9]2[S:10][CH:11]=[C:7]([CH3:6])[N:8]=2)([OH:18])[CH3:17])=[C:20]([CH3:25])[N:21]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5208882,4-Dimethyl-5-acetylthiazoleHCID 116583544-Methyl-2-trimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 229151551-(2,4-Dimethyl-5-thiazolyl)-1-(4-methyl-2-thiazolyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexanes, 5.1 ml ) was added dropwise to a stirred solution of 4-methyl-2-trimethylsilylthiazole (from 4-methylthiazole, n-butyllithium and trimethylsilylchloride) (2 g) in anhydrous tetrahydrofuran (40 ml ) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 5-acetyl-2,4-dimethylthiazole (2 g) in tetrahydrofuran (10 ml) was added dropwise. After 1 hour the mixture was allowed to warm to room temperature. After a further 2 hours, saturated aqueous ammonium chloride solution was added. The organic phase was separated, washed, dried and evaporated. The residue was dissolved in tetrahydrofuran (2 ml) and tetrabutylammonium fluoride (640 mg) was added. The mixture was stirred overnight and then worked up in the usual fashion to give the title compound.

Workup

  1. waitAfter 1 hour the mixture was allowed
  2. waitAfter a further 2 hours
  3. customThe organic phase was separated
  4. washwashed
  5. customdried
  6. customevaporated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (2 ml)
  8. additiontetrabutylammonium fluoride (640 mg) was added

Sources & evidence

ORD record
ord-0fd3b3e7f93243418bdb481a70895a1b
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

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