Ethylene Glycol → HCID 86591408, 화합물

HRID 2220160노트

반응식

HRID 2220160 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1.[CH2:18](O)[CH2:19][OH:20]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:20]1[C:2]2([CH2:6][CH2:5][N:4]([S:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)(=[O:9])=[O:8])[CH2:3]2)[O:1][CH2:18][CH2:19]1

참가 물질

5

반응물 2

HCID 174Ethylene GlycolHCID 67354698HCID 67354698, 화합물

생성물 1

HCID 86591408HCID 86591408, 화합물수율 96%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene용매

실험 절차

4-[(3-oxo-1-pyrrolidinyl)sulfonyl]benzonitrile 23b (11.6 g, 46.3 mmol) was suspended in toluene (110 ml) and stirred at room temp. Ethylene glycol (6.2 ml, 6.9 g, 111 mmol) and para-toluene sulphonic acid monohydrate (100 mg, 0.53 mmol) were added. The reaction mixture was heated to reflux under Dean-Stark conditions and monitored by water collection and TLC (5% methanol in DCM). If necessary for the completion of the reaction (typically within 3h), further portions of p-TSA were added. When complete the reaction mixture was washed with saturated sodium bicarbonate solution (55 ml) and water (2×55 ml). The organic layer was filtered through cotton wool and then concentrated in vacuo to approximately 50 ml or until precipitation started. Hexane (150 ml) was added and the suspension stirred at 0-5° C. for 10-20 min, filtered and washed with hexane (2×50 ml). The residue was air dried to yield 13.0 g (96%) ketal 4-(1,4-dioxa-7-azaspiro[4.4]non-7-ylsulfonyl)benzonitrile 23c.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under Dean-Stark conditions
  3. custommonitored by water collection and TLC (5% methanol in DCM)
  4. customIf necessary for the completion of the reaction (typically within 3h), further portions of p-TSA
  5. additionwere added
  6. washWhen complete the reaction mixture was washed with saturated sodium bicarbonate solution (55 ml) and water (2×55 ml)
  7. filtrationThe organic layer was filtered through cotton wool
  8. concentrationconcentrated in vacuo to approximately 50 ml or until precipitation
  9. additionHexane (150 ml) was added
  10. stirringthe suspension stirred at 0-5° C. for 10-20 min
  11. filtrationfiltered
  12. washwashed with hexane (2×50 ml)
  13. customdried

출처 및 근거

ORD 기록
ord-f92cb459754e4bcab34cea426d2f7397
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417058B2

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