1,6-Dibromohexane → HCID 19876761, compound

HRID 1886015Notes

Reaction equation

HRID 1886015 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][OH:9])[N:6]=1.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>O>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:9][CH2:8][CH2:7][C:5]1[N:6]=[C:2]([CH3:1])[S:3][CH:4]=1

Participants

4

Reactant 2

HCID 123681,6-DibromohexaneHCID 198767392-(2-Methyl-1,3-thiazol-4-yl)ethan-1-ol

Product 1

HCID 19876761HCID 19876761, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methyl-4-thiazoleethanol (2.22 g), 1,6-dibromohexane (7.1 ml) 12.5M aqueous sodium hydroxide (4 ml) and TAB (0.1 g) was stirred rapidly at room temperature for 16 h. The reaction mixture was diluted with water (30 ml), extracted with ether (3×30 ml) and the combined organic extracts were washed with water (30 ml) and brine (30 ml), dried and concentrated. The residual oil was purified by FCC eluting with diethyl ether-hexane (1:3) to give the title compound as an orange oil (2.21 g), t.l.c. (ether-hexane 1:3) Rf 0.17

Workup

  1. extractionextracted with ether (3×30 ml)
  2. washthe combined organic extracts were washed with water (30 ml) and brine (30 ml)
  3. customdried
  4. concentrationconcentrated
  5. customThe residual oil was purified by FCC
  6. washeluting with diethyl ether-hexane (1:3)

Sources & evidence

ORD record
ord-61af359a52464286bebb9a9858be5a41
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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