(Diethylamino)sulfur trifluoride → HCID 59699468、化合物

HRID 901083ノート

反応式

HRID 901083 の反応式
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:16])=O)=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1.C(N(S(F)(F)[F:29])CC)C>ClCCl>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:16][F:29])=[CH:10][CH:9]=2)[O:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4]1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59699464HCID 59699464、化合物

生成物 1

HCID 59699468HCID 59699468、化合物収率 93.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

To a solution of 20 (390.9 g, 1.11 mol) and SbCl3 (7.62 g, 0.0334 mol) in anhydrous dichloromethane (2.27 L) at −15° C., diethylamino sulfurtrifluoride (DAST) (258 ml, 2.0 mol) was added drop-wise. The reaction mixture was stirred for 3 hours at −20° C. and then allowed to warm up to room temperature overnight. The reaction was quenched with 1N NaOH solution until pH=3-4 at −20° C., and then solid NaHCO3 was added to pH=8. The organic layer was separated and the aqueous solution was extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated to provide 330 g of the desired product as a brown oil.

後処理

  1. temperatureto warm up to room temperature overnight
  2. customThe reaction was quenched with 1N NaOH solution until pH=3-4 at −20° C.
  3. additionsolid NaHCO3 was added to pH=8
  4. customThe organic layer was separated
  5. extractionthe aqueous solution was extracted with dichloromethane
  6. washThe combined organic extracts were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-67be831b45aa455f810b4e65e57d149c
出典データセット
uspto-grants-2008_04
特許番号
US07361689B2

反応ノート

読み込み中…