p-Toluenesulfonic acid → HCID 59342358、化合物

HRID 15730

反応式

HRID 15730 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 59342358HCID 59342358、化合物収率 81%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee9130598be74c03a5d2ba3e8c103572
出典データセット
uspto-grants-2010_06
特許番号
US07732609B2

関連ノート

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