Methyl Acetate → 5-Chlorothiophene-2-Sulfonamide

HRID 1271662Notes

Reaction equation

HRID 1271662 reaction equation
C(OC)(=O)C.[Cl:6][C:7]1[S:11][C:10]([S:12]([NH:15]C2C3CCC2(C(O)=O)CC2C=CC=CC=2C3)(=[O:14])=[O:13])=[CH:9][CH:8]=1.C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1.CN(C=O)C>[Cl:6][C:7]1[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6584Methyl AcetateHCID 65578Oxalyl chlorideHCID 131726338HCID 131726338, compound

Product 1

HCID 12413015-Chlorothiophene-2-SulfonamideYield 112.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

To a suspension of (6R/S,9R/S,11S/R)-11-{[(5-chlorothien-2-yl)sulfonyl]amino}-7,8,9,10-tetrahydro-6,9-methanobenzo[α][8]annulene-6(5H)-carboxylic acid (example 3, Step (1)) (100 mg) in benzene (3 ml) were added oxalyl chloride (74 μl) and DMF (1 drop) at room temperature and the mixture stirred for 2 hrs. After concentration in vacuo, the residue was redissolved in benzene (3 ml) and added dropwise to a refluxing suspension of N-hydroxypyridin-2-thione sodium salt (43 mg) in CBrCl3 (4 ml) whilst irradiating with a 250 W lamp for 1 hr. Concentration and purification using HPLC gave N-[(6R/S,9R/S,11S/R)-6-bromo-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[α][8]annulen-11-yl]-5-chlorothiophene-2-sulfonamide as a white solid (54 mg, 50%).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was redissolved in benzene (3 ml)
  3. additionadded dropwise to a refluxing suspension of N-hydroxypyridin-2-thione sodium salt (43 mg) in CBrCl3 (4 ml)
  4. customwhilst irradiating with a 250 W lamp for 1 hr
  5. concentrationConcentration and purification

Sources & evidence

ORD record
ord-4ffb48a32c654b04926895934bca2c98
Source dataset
uspto-grants-2007_04
Patent number
US07205434B2

Reaction notes

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