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

HRID 729260ノート

反応式

HRID 729260 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-96e07fbadc31472abab737d3795488c5
出典データセット
uspto-grants-2009_09
特許番号
US07582629B2

反応ノート

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