2-Methyl-2-nitro-1,3-propanediol → 2-Methyl-2-nitro-1,3-propanediol-di-p-toluenesulfonate

HRID 660123

반응식

HRID 660123 반응식
[CH3:1][C:2]([N+:7]([O-:9])=[O:8])([CH2:5][OH:6])[CH2:3][OH:4].C(N([CH2:15][CH3:16])CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(OCC)C>[S:17]([O:4][CH2:3][C:2]([CH3:1])([N+:7]([O-:9])=[O:8])[CH2:5][O:6][S:17]([C:16]1[CH:15]=[CH:24][C:23]([CH3:25])=[CH:22][CH:21]=1)(=[O:19])=[O:18])([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

참가 물질

5

반응물 3

HCID 64802-Methyl-2-nitro-1,3-propanediolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

생성물 1

HCID 5195532-Methyl-2-nitro-1,3-propanediol-di-p-toluenesulfonate수율 5.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 2-methyl-2-nitro-1,3-propanediol (80 g, 0.592 mol) and triethylamine (131.8 g, 1.303 mol) in diethyl ether (250 ml) is added a solution of tosyl chloride (225.7 g, 1.184 mol) in diethyl ether (800 ml) between −15° and −20° C. The resulting suspension is stirred at 0° C. for 1 hour, then 18 hours at ambient temperature. The reaction mixture is filtered, the solid residue is taken up twice in ethyl acetate and stirred, the suspension being filtered again. The combined ethyl acetate layers are evaporated to dryness giving a first crop of crude product (175.8 g). The ether filtrate is washed with water (2×) and brine, dried (Na2SO4), filtered, and partly concentrated. The suspension is filtered giving another 15.0 g of product. The crude solid product (190.8 g, 73%) is used in the next step without further purification.

후처리

  1. custom18 hours
  2. customat ambient temperature
  3. filtrationThe reaction mixture is filtered
  4. stirringstirred
  5. filtrationthe suspension being filtered again
  6. customThe combined ethyl acetate layers are evaporated to dryness
  7. customgiving a first crop of crude product (175.8 g)
  8. washThe ether filtrate is washed with water (2×) and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationpartly concentrated
  12. filtrationThe suspension is filtered

출처 및 근거

ORD 기록
ord-c9ed6bd26b3d48ca960346c188f758b7
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084474B2

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