Dichloromethane → HCID 22277825, compound

HRID 2055309Notes

Reaction equation

HRID 2055309 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([C:16]([NH:18][C:19]1[CH:31]=[CH:30][C:22]2[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:21]=2[CH:20]=1)=[O:17])([CH3:15])([CH3:14])[CH3:13].C(Cl)Cl>ClCCCl>[O:6]=[S:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:21]2[CH:20]=[C:19]([NH:18][C:16]([C:12]([CH3:15])([CH3:13])[CH3:14])=[O:17])[CH:31]=[CH:30][C:22]1=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 22277799HCID 22277799, compound

Product 1

HCID 22277825HCID 22277825, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (50% wt/wt, 770 mg, 2.0 mmol) was added to a solution of 2-(t-butylcarbonylamino)dibenzothiophene (Example 2; 566 mg, 2.0 mmol) in 1,2-dichloroethane and the resultant mixture warmed at 80% for 16 hours then cooled and DCM was added (50 ml). The mixture was washed with 2 M sodium hydroxide, water and brine, dried and evaporated in vacuo to a brown gum. This was purified by chromatography eluting with 0-2% methanol in DCM. The impure product thus obtained was purified by preparative HPLC (Dynamax C-18 60A column eluted with 40-95% acetonitrile in water plus 0.1% trifluoroacetic acid) to obtain the product (53.5 mg) NMR: 9.59 (s, 1H), 8.35 (d, 1H), 8.03 (d, 1H), 7.97 (d, 1H), 7.93 (d, 1H), 7.80 (dd, 1H), 7.70 (t, 1H), 7.56 (t, 1H), 1.16 (s, 9H); m/z 300.

Workup

  1. temperaturethen cooled
  2. washThe mixture was washed with 2 M sodium hydroxide, water and brine
  3. customdried
  4. customevaporated in vacuo to a brown gum
  5. customThis was purified by chromatography
  6. washeluting with 0-2% methanol in DCM
  7. customThe impure product thus obtained
  8. customwas purified by preparative HPLC (Dynamax C-18 60A column eluted with 40-95% acetonitrile in water plus 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-839846bf3d0b4767b1e743b6c93036f2
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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