Imidazole → HCID 20084330, compound

HRID 327560Notes

Reaction equation

HRID 327560 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 20084330HCID 20084330, compoundYield 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-a3337543c5ce4792baeb4255a9150f21
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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