HCID 19106478, compound → HCID 19106469, compound

HRID 1197435Notes

Reaction equation

HRID 1197435 reaction equation
C[Li].[CH3:3]COCC.CN(OC)[C:10]([C:12]1[CH:16]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:14][C:13]=1[Cl:21])=[O:11]>C1COCC1>[C:10]([C:12]1[CH:16]=[C:15]([S:17]([NH2:18])(=[O:20])=[O:19])[S:14][C:13]=1[Cl:21])(=[O:11])[CH3:3]

Participants

4

Reactant 2

HCID 19106478HCID 19106478, compoundHCID 178467906HCID 178467906, compound

Product 1

HCID 19106469HCID 19106469, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.5M methyllithium/ether (26 mL, 0.039 mol) was added dropwise to a solution of N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamide (3.25 g, 0.011 mol) in dry THF (145 mL) under a nitrogen atmosphere, cooled to -78° C. After two hours, the reaction mixture was poured carefully into ice/dil. HCl and the product was extracted into ethyl acetate. This extract was washed with water and brine, dried (Na2SO4), filtered and evaporated to give 2.82 g of crude solid product. This material was chromatographed on silica gel and eluted with 40% ethyl acetate/hexane to give 1.7 g (74%) of product. Recrystallization from ethyl acetate/hexane gave 1.68 g of product, mp 128°-130° C.

Workup

  1. additionthe reaction mixture was poured carefully into ice/dil
  2. extractionHCl and the product was extracted into ethyl acetate
  3. washThis extract was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give 2.82 g of crude solid product
  8. customThis material was chromatographed on silica gel
  9. washeluted with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a0902973f10e4932823b0ae2b6ca229c
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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