Triethylamine → N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide

HRID 729260노트

반응식

HRID 729260 반응식
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH2:20]([S:27](Cl)(=[O:29])=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:27]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 20633524-(Difluoromethoxy)benzylamine

생성물 1

HCID 33038515N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide수율 92.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-(Difluoromethoxy)benzyl amine (1.73 g, 9.97 mmol) was dissolved in THF (10 mL). It was cooled in an ice-bath. Under nitrogen atmosphere, triethylamine (1.46 mL, 10.46 mmol) was added and then benzylsulfonyl chloride (1.9 g, 9.97 mmol) in THF (10 mL) was dropped in. The cooling bath was removed after the addition. The mixture was stirred for 3 h and then evaporated to dryness. DCM (50 mL) was added to the residue. It was then washed with 1% HCl (15 mL), water (50 mL×3) and brine, dried (MgSO4) and evaporated to give the title compound (3.01 g. 92%) as a solid; 1H NMR (400 MHz, CDCl3): δ 7.32-7.40 (m, 5H), 7.26 (d, 2H), 7.09 (d, 2H), 6.49 (t, 1H), 4.36 (bt, 1H), 4.24 (s, 2H), 4.10 (d, 2H); Mass Spectrum: M−H+ 326.

후처리

  1. temperatureIt was cooled in an ice-bath
  2. customThe cooling bath was removed
  3. additionafter the addition
  4. customevaporated to dryness
  5. additionDCM (50 mL) was added to the residue
  6. washIt was then washed with 1% HCl (15 mL), water (50 mL×3) and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

출처 및 근거

ORD 기록
ord-96e07fbadc31472abab737d3795488c5
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582629B2

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