(Diethylamino)sulfur trifluoride → HCID 59699468, 화합물

HRID 901083노트

반응식

HRID 901083 반응식
[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

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59699464HCID 59699464, 화합물

생성물 1

HCID 59699468HCID 59699468, 화합물수율 93.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67be831b45aa455f810b4e65e57d149c
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361689B2

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