p-Toluenesulfonic acid → HCID 59342358, 화합물

HRID 15730

반응식

HRID 15730 반응식
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16](/[N:19]=[CH:1]/[C:3]2[CH:4]=[N:5][CH:6]=[N:7][CH:8]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 668244-ChlorobenzenesulfonamideHCID 2761034Pyrimidine-5-carboxaldehyde

생성물 1

HCID 59342358HCID 59342358, 화합물수율 81%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 5-formyl pyrimidine (68, 1.0 g, 9.3 mmol) and 4-chlorobenzene sulfonamide (1.95 g, 10.2 mmol) in toluene (20 mL) was added 4 Å molecular sieves (1.0 g) and MP-TsOH (1.0 g). Dean-stark apparatus with reflux condenser was affixed to reaction vessel and reaction was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and filtered through Celite. The filtrate was concentrated in vacuo to yield 2.12 g (81%) 69 as a light brown solid, 1H NMR (CDCl3) δ 9.42 (s, 1H), 9.25 (s, 2H), 9.15 (s, 1H), 7.98 (d, 2H), 7.57 (d, 2H).

후처리

  1. temperatureDean-stark apparatus with reflux condenser
  2. customwas affixed to reaction vessel and reaction
  3. temperaturewas heated
  4. temperatureat reflux for 18 hours
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-ee9130598be74c03a5d2ba3e8c103572
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732609B2

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