Sodium hydride → HCID 24964377, 화합물

HRID 2425062노트

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HRID 2425062 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 24964377HCID 24964377, 화합물수율 45.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-1abf1a4a8c6947b9a485028dc7bc6ceb
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964633B2

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