Methyl iodide → HCID 19384301, compound

HRID 2399731Notes

Reaction equation

HRID 2399731 reaction equation
[F:1][C:2]([F:19])=[CH:3][CH2:4][CH2:5][S:6][C:7]1[O:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:10]=2[N:11]=1.[C:20](=O)([O-])O.[Na+].CI>CN(C)C=O.CCOCC>[F:19][C:2]([F:1])=[CH:3][CH2:4][CH2:5][S:6][C:7]1[O:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:20])=[O:17])=[CH:12][C:10]=2[N:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 19384328HCID 19384328, compound

Product 1

HCID 19384301HCID 19384301, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(4,4-difluorobut-3-enylthio)benzoxazole-5-carboxylic acid (400 mg) in dimethylformamide (5 cm3) was added sodium hydrogen carbonate (224 mg) and methyl iodide (284 mg). The reaction mixture was stirred at the ambient temperature for 1 hour. The reaction mixture was filtered through High-flo to remove solid material and the filtrate evaporated to give a yellow oil. This oil was taken up in ether and washed with water. The ether was dried (MgSO4) and evaporated to give a yellow oil when crystallised on standing. Recrystallisation from hexane gave methyl 2-(4,4-difluorobut-3-enylthio)benzoxazole-5-carboxylate as a white solid (31 mg). 1H NMR (CDCl3): δ8.29(1H,d); 8.03(1H,dd); 7.48(1H,d); 4.32(1H,ddt); 3.94(3H,s); 3.36(2H,t); 2.58(2H bq).

Workup

  1. filtrationThe reaction mixture was filtered through High-flo
  2. customto remove solid material
  3. customthe filtrate evaporated
  4. customto give a yellow oil
  5. washwashed with water
  6. dry with materialThe ether was dried (MgSO4)
  7. customevaporated
  8. customto give a yellow oil when
  9. customcrystallised
  10. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-146953b1339644a09a42e264b0194d17
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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