Potassium Carbonate → 6-(4-Methylthiazol-2-yl)thiohexan-1-ol

HRID 892748Notes

Reaction equation

HRID 892748 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][C:5]1[N:6]=[C:2]([S:1][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 1784319804-methyl-1,3-thiazole-2-thiol

Product 1

HCID 198940506-(4-Methylthiazol-2-yl)thiohexan-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 2-mercapto-4-methylthiazole (2.62 g, 0.02 mol), 6-bromo-1-hexanol (3.62 g, 0.02 mol), potassium carbonate (2.76 g, 0.02 mol) and acetone (50 mL) was refluxed for 14 h. After cooling, the mixture was filtered and the filtrate was evaporated. The residual oil was purified by elution from a silica gel column using ethylacetate-methanol (99:1, v./v) as eluant to give 6-(4-methylthiazol-2-yl)thiohexan-1-ol (29) (99%) as a yellowish oil. IR (neat) 3608 (OH)cm-1 ; NMR (CDCl3) 1.25-2.10 (m, 8H, (CH2)4), 2.38 (S, 3H, Me-Het), 3.18 (t, J=9 Hz, 2H, CH2 --S), 3 65 (t, J=9 Hz, 2H, CH2 --O), 6.75 (S, 1H, H-Het). Analysis found: C, 51.98; H, 7.49; N, 5.92; S, 27.65. Required: C, 51.90; H, 7.40; N, 6.08; S, 27.71 (C10H17NOS2). ##STR11##

Workup

  1. temperaturewas refluxed for 14 h
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residual oil was purified by elution from a silica gel column

Sources & evidence

ORD record
ord-0a2ea6b803a6411c9ace19630ff7d4c5
Source dataset
uspto-grants-1992_06
Patent number
US05120750

Reaction notes

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