Water → HCID 59393586, compound

HRID 660131Notes

Reaction equation

HRID 660131 reaction equation
FC(F)(F)C(O)=O.[O:8]=[S:9]1(=[O:15])[CH2:12][C:11]([CH3:14])([NH2:13])[CH2:10]1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH3:36])[C:27]([N:33]=S=O)=[C:28]([CH:32]=1)[C:29](Cl)=[O:30].O>O1CCCC1>[NH2:33][C:27]1[C:26]([CH3:36])=[CH:25][C:24]([Cl:23])=[CH:32][C:28]=1[C:29]([NH:13][C:11]1([CH3:14])[CH2:12][S:9](=[O:15])(=[O:8])[CH2:10]1)=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 569495305-Chloro-3-methyl-2-(sulfinylamino)benzoyl chlorideHCID 66823233HCID 66823233, compound

Product 1

HCID 59393586HCID 59393586, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1-dioxo-3-methyl-3-thietanamine trifluoroacetic acid salt [the product of step 1] (598 mg, 2.40 mmol) and triethylamine (0.836 ml, 6.00 mmol) in tetrahydrofuran (6 ml) cooled at 0-5° C. is added a solution of 5-chloro-3-methyl-2-sulfinylaminobenzoyl chloride [the product of step 2] (600 mg, 2.4 mmol) in tetrahydrofuran (4 ml). The reaction mixture is stirred at room temperature overnight, and then poured into water. After extraction with ethyl acetate, the combined organic layers are washed with brine, dried (Na2SO4), filtered and concentrated. The crude product is purified by column chromatography on silica gel (ethyl acetate/hexane 1:4) to afford the title benzamide [compound D54 from Table D] (410 mg, 56%) as a white solid with a melting point of 79-82° C.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography on silica gel (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-c106c2e0aded4c25b8ed9949dd869e36
Source dataset
uspto-grants-2011_12
Patent number
US08084474B2

Reaction notes

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