Imidazole → 2-Iodomethyl-4-(1-methylethyl)thiazole

HRID 1609322Notes

Reaction equation

HRID 1609322 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([CH2:9]O)[S:7][CH:8]=1)[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:35]I>C1(C)C=CC=CC=1>[I:35][CH2:9][C:6]1[S:7][CH:8]=[C:4]([CH:2]([CH3:3])[CH3:1])[N:5]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10678505(4-Isopropylthiazol-2-yl)methanol

Product 1

HCID 200843302-Iodomethyl-4-(1-methylethyl)thiazoleYield 117.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture composed of 2.5 g of 4-(1-methylethyl)thiazole methanol, 6.3 g of triphenylphosphine, 2.2 g of imidazole and 100 ml of toluene was warmed until all of the solids dissolved. This solution was cooled to 10° C. and 6.1 g of iodine was added. After 2 hr, the mixture was washed with an excess of sodium thiosulfate solution. The aqueous layer was back extracted with ethyl ether and the combined organic layers were washed with brine and then dried (MgSO4). Removal of the solvents in vacuo yielded 5.0 g of 2-iodomethyl-4-(1-methylethyl)thiazole as an oil.

Workup

  1. temperaturewas warmed until all of the solids
  2. dissolutiondissolved
  3. washthe mixture was washed with an excess of sodium thiosulfate solution
  4. extractionThe aqueous layer was back extracted with ethyl ether
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-77bf6b619b9349ba8f10284bff8d6d7e
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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