Chloroform → HCID 54251365, compound

HRID 569017Notes

Reaction equation

HRID 569017 reaction equation
C([O:4][C@@H:5]1[C@H:9]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[S:8](=O)[C:7]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:6]1=2)C=C.FC(F)(F)C(O[C:27](=O)[C:28](F)(F)F)=O.[CH:35](Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:35]([C:9]1([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[S:8][C:7]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:6]=2[C:5]1=[O:4])[CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 9845Trifluoroacetic anhydrideHCID 53663786HCID 53663786, compound

Product 1

HCID 54251365HCID 54251365, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reflux 15.2 g (47.1 mmole) of cis 3-allyloxy-6-chloro-2,3-dihydro-2-(1H-1-imidazolylmethyl)benzo[b]thiophene-1-oxide and 9.97 mL (70.6 mole) of trifluoroacetic anhydride in 150 mL of toluene for 1 hr. Pour the reaction mixture into 1 liter of CHCl3 and extract it with 1 liter of 5% aqueous Na2CO3 followed by 1 liter of H2O. Dry the organic layer over anhydrous MgSO4 and evaporate the solvent in vacuo. Chromatograph the oily residue on 500 g of silica gel eluting with CHCl3 to give 2-allyl-6-chloro-2,3-dihydro-2-(1H-1-imidazolylmethyl) benzo[b]thiophene-3-one, a gum, m/e 304.

Workup

  1. extractionextract it with 1 liter of 5% aqueous Na2CO3
  2. dry with materialDry the organic layer over anhydrous MgSO4
  3. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-a865a589819549aaa937a68bb1a738b7
Source dataset
uspto-grants-1988_03
Patent number
US04731364

Reaction notes

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