Sodium Carbonate → HCID 178493185, compound

HRID 1789043Notes

Reaction equation

HRID 1789043 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([F:38])([O:17][C:18]1[CH:37]=[CH:36][C:21]2[NH:22][C:23]([S:25][CH:26]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][N:29]=3)[CH3:27])=[N:24][C:20]=2[CH:19]=1)[CH:14]([F:16])[F:15].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:38][C:13]([F:12])([O:17][C:18]1[CH:37]=[CH:36][C:21]2[NH:22][C:23]([S:25]([CH:26]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][N:29]=3)[CH3:27])=[O:6])=[N:24][C:20]=2[CH:19]=1)[CH:14]([F:15])[F:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 178493184HCID 178493184, compound

Product 1

HCID 178493185HCID 178493185, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

9.8 g of 80% m-chloroperoxybenzoic acid in 200 ml of dichloromethane are added dropwise at -65° C. to a solution of 19.5 g of ±-5-(1,1,2,2-tetrafluoroethoxy)-2-{[1-(4-methoxy-2-pyridyl)ethyl]thio}-1H-benzimidazole in 1.5 l of dichloromethane. The reaction mixture is stirred for a further 2 h at -40° C. and then stirred into a sodium carbonate solution. The organic phase is separated off, and the aqueous phase is extracted once more with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated. A sparingly soluble diastereomer thus crystallises. The other diastereomer remains in the mother liquor and can either be purified by chromatography or can, by leaving it to stand, preferably in the presence of bases, be rearranged into the less soluble diastereomer. Recrystallisation of sparingly soluble product from ethyl acetate/diisopropyl ether gives 10 g (51%) of the title compound of m.p. 156°-157° C.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted once more with dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated
  5. customA sparingly soluble diastereomer thus crystallises
  6. customcan either be purified by chromatography
  7. customcan, by leaving it
  8. customRecrystallisation of sparingly soluble product from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-701b9f38ff994ea8ba273450e05ee229
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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