1,6-Dibromohexane → HCID 19876761, compound

HRID 982381Notes

Reaction equation

HRID 982381 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 eter-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 eter-hexane (1:3)

Sources & evidence

ORD record
ord-c15d672bef7b4b1895948e29dd3a2922
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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