Sodium hydride → N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea

HRID 1602554노트

반응식

HRID 1602554 반응식
[CH2:1]([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>CN(C=O)C>[CH3:23][CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:31])[CH3:32])[C:25]=1[NH:33][C:34]([NH:18][S:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:16])=[O:17])=[O:35])[CH3:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 922592,6-Diisopropylphenyl isocyanateHCID 196118321-Tetradecylsulfonamide

생성물 1

HCID 19611841N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea수율 62.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 1-tetradecylsulfonamide (9.0 g, 32.4 mmoles) in DMF (90 mL) was added dropwise to a stirred suspension of NaH (1.63 g, 68 mmoles) in 30 mL of DMF. The solution was stirred 60 minutes, then 2,6-diisopropylphenyl isocyanate (7.0 mL, 33 mmoles) was added dropwise. The mixture was stirred overnight at room temperature, then quenched by dropwise addition of 1M HCl. The mixture was then partitioned between H2O and ethyl acetate (500 mL each). The aqueous layer was further extracted with ethyl acetate. The combined ethyl acetate extracts were diluted with hexane (100 mL) and then washed exhaustively with H2O. The organic extracts were dried, filtered, and concentrated to a solid residue, which was triturated with ether and the solid isolated by suction filtration and dried. Isolated 9.70 g of solid, m.p. 135-137° C.

후처리

  1. stirringThe mixture was stirred overnight at room temperature
  2. customquenched by dropwise addition of 1M HCl
  3. customThe mixture was then partitioned between H2O and ethyl acetate (500 mL each)
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. additionThe combined ethyl acetate extracts were diluted with hexane (100 mL)
  6. washwashed exhaustively with H2O
  7. customThe organic extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated to a solid residue, which
  10. customwas triturated with ether
  11. customthe solid isolated by suction filtration
  12. customdried

출처 및 근거

ORD 기록
ord-8c67cb6dd65a40d8a474359c2e558410
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981595

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