Water → HCID 19045060、化合物

HRID 1781235ノート

反応式

HRID 1781235 の反応式
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[NH2:18].O.[Cl-].[Na+]>CN(C)C1C=CN=CC=1.O1CCCC1.ClCCCC>[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[NH:18][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]

参加物

8

反応物 4

HCID 962Water2 回HCID 5234Sodium ChlorideHCID 12661DiketeneHCID 27753062-Bromo-4-methyl-6-nitroaniline

生成物 1

HCID 19045060HCID 19045060、化合物収率 46%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8005Butyl Chloride溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of diketene (57.71 mL, 748.2 mmol) was added dropwise over 2 h to a stirred solution of title compound of Step A (34.57 g, 149.6 mmol) and 4-dimethylaminopyridine (914 mg, 7.48 mmol) in dry tetrahydrofuran (450 mL) at room temperature under a nitrogen atmosphere. The reaction was allowed to stir at room temperature overnight. First, water was added to the reaction, and then the reaction mixture was poured into water. The mixture was saturated with sodium chloride and was extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give a brown oil. The brown oil was suspended in 1-chlorobutane. The resultant precipitate was filtered from this suspension to afford the title compound of Step B as a brown solid melting at 136°-138° C. (21.67 g, 46%). 1H NMR (CDCl3): δ2.35 (s,3H), 2.41 (s,3H), 3.63 (s,2H), 7.69 (s,2H), 9.6 (br s, 1H).

後処理

  1. extractionwas extracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto give a brown oil
  6. filtrationThe resultant precipitate was filtered from this suspension

出典と根拠

ORDレコード
ord-8b376187240b4ed782555b182275be4f
出典データセット
uspto-grants-1997_05
特許番号
US05633218

反応ノート

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