Sodium hydride → HCID 24964377, compound

HRID 2425062Notes

Reaction equation

HRID 2425062 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.[H-].[Na+].[CH2:13]([N:23]=[C:24]=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22]>CN(C)C=O>[CH2:13]([NH:23][C:24]([NH:10][S:7]([C:4]1[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=1)(=[O:9])=[O:8])=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH:10][S:7]([C:4]1[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=1)(=[O:9])=[O:8])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124961361,7-DiisocyanatoheptaneHCID 572350435-Methylthiophene-3-sulfonamide

Product 1

HCID 24964377HCID 24964377, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.35 g 5-methyl-thiophene-3-sulfonic acid amide (example 46a) in 10 ml dimethylformamide was added 0.080 g sodium hydride 55% in oil and the mixture was stirred at room temperature for 30 min. To the resulting solution was added dropwise 0.180 g heptamethylene diisocyanate (CAS18020-78-5) and the mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was washed with ethyl acetate and purified by chromatography on 100 ml MCl gel with a gradient (water 0-50% acetonitrile) The product fractions were collected and the product was precipitated by adjusting the pH to 2.00 by addition of 1N hydrochloric acid. The solid was collected by filtration and washed with water and dried to constant weight to yield 0.24 g of the title compound as white powder. MS (ISN) M−H+=536.0

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. washthe aqueous phase was washed with ethyl acetate
  6. custompurified by chromatography on 100 ml MCl gel with a gradient (water 0-50% acetonitrile) The product fractions
  7. customwere collected
  8. customthe product was precipitated
  9. additionby addition of 1N hydrochloric acid
  10. filtrationThe solid was collected by filtration
  11. washwashed with water
  12. customdried to constant weight

Sources & evidence

ORD record
ord-1abf1a4a8c6947b9a485028dc7bc6ceb
Source dataset
uspto-grants-2011_06
Patent number
US07964633B2

Reaction notes

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