Tributylstannane → HCID 13508144, compound

HRID 1449396Notes

Reaction equation

HRID 1449396 reaction equation
Br[CH:2]([F:28])[C:3]([F:27])([F:26])[S:4][C:5]1[NH:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:7]2[N:6]=[C:5]([S:4][C:3]([F:27])([F:26])[CH2:2][F:28])[NH:9][C:8]=2[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 5948Tributylstannane2×HCID 13508095HCID 13508095, compound

Product 1

HCID 13508144HCID 13508144, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(2-bromo-1,1,2-trifluoroethylthio)-4,5-bis(4-methoxyphenyl)imidazole (14.2 g., 0.03 mole) in 150 ml. toluene is added tri-n-butyltin hydride (9.0 g., 0.03 mole). The mixture is refluxed for four hours. Another 9.0 g. (0.03 mole) of tri-n-butyltin hydride is added and the mixture is refluxed overnight. The mixture is then added directly to a column of 2 lb. of silica gel (SilicAR® CC-7). Elution with toluene followed by toluene/ethyl acetate (95/5) gives 6.5 g. of crystalline product. A recrystallization from methylcyclohexane gives 5.6 g. of pure product, m.p. 143.5°-145°.

Workup

  1. temperatureThe mixture is refluxed for four hours
  2. temperaturethe mixture is refluxed overnight
  3. additionThe mixture is then added directly to a column of 2 lb
  4. washElution with toluene
  5. customgives 6.5 g
  6. customA recrystallization from methylcyclohexane
  7. customgives 5.6 g

Sources & evidence

ORD record
ord-a03a9e1f2f454603bf91b4c4d683b258
Source dataset
uspto-grants-1980_02
Patent number
US04190666

Reaction notes

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