Sulfuric Acid → gamma-Cyhalothrin

HRID 2377128

반응식

HRID 2377128 반응식
[CH3:1][C:2]1([CH3:31])[CH:4]([C:5]([O:7][CH:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[C:9]#[N:10])=[O:6])[CH:3]1/[CH:24]=[C:25](\[Cl:30])/[C:26]([F:29])([F:28])[F:27].C(NC(C)C)(C)C.S(=O)(=O)(O)O>C(O)(C)C.CCCCCC.O>[CH3:1][C:2]1([CH3:31])[C@H:4]([C:5]([O:7][C@@H:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[C:9]#[N:10])=[O:6])[C@@H:3]1/[CH:24]=[C:25](\[Cl:30])/[C:26]([F:27])([F:29])[F:28]

참가 물질

7

반응물 3

HCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 5281873Cyhalothrin

생성물 1

HCID 6440554gamma-Cyhalothrin

시약·촉매·용매 3

HCID 962Water용매2회HCID 3776Isopropanol용매HCID 8058Hexane용매2회

반응 조건

온도
-5 °C

실험 절차

A 600 ml vacuum jacketed non-baffled split-neck reaction flask was equipped with a dual blade agitator. To the reactor, already containing a slurry of epimerisation mass as seed from a previous experiment (already˜⅔rds full), was charged the 1 R cyhalothrin (II) (166.3 g) in a mixture of isopropanol (99.9 g), water (3.09 g) and di-isopropylamine (5.22 g). The reaction mass was agitated at 100 rpm and −5° C. for 65 hr, before removing 251 g of reaction mass and transferring it to a 1 liter split-neck reaction vessel in an ice/water bath. To the 1 liter reaction vessel was charged hexane (60 ml) and sulphuric acid (47 ml of 50% w/w), and the resultant thick paste was agitated for 0.5 hr before diluting with hexane (350 ml) and water (350 ml). The mixture was heated to 55° C. for 30 min, then transferred to a separating funnel and the lower aqueous phase was separated off. The hexane solution was concentrated under reduced pressure to give the desired product as a viscous red/brown oil which solidified upon standing to give an off-white solid. The product weighed 151.2 g giving an estimated yield of 97% as gamma-cyhalothrin and a diastereomer ratio of 95:5.

후처리

  1. customwas equipped with a dual blade agitator
  2. additionTo the reactor, already containing a slurry of epimerisation mass as seed from a previous experiment (already˜⅔rds full),
  3. custombefore removing
  4. custom251 g of reaction mass
  5. customTo the 1 liter reaction vessel
  6. stirringthe resultant thick paste was agitated for 0.5 hr
  7. temperatureThe mixture was heated to 55° C. for 30 min
  8. customtransferred to a separating funnel
  9. customthe lower aqueous phase was separated off
  10. concentrationThe hexane solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-01413736130d4c9d87d2a2ccf9c58d48
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468453B2

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