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Tert-butyl 4-formylbenzoate → HCID 178450684、化合物

HRID 1486570
ノート
印刷プレビュー

反応式

HRID 1486570 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:16]([O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=1)([CH3:19])([CH3:18])[CH3:17].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:28][C:25]3[CH:26]=[CH:27][C:22]([C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:30])=[CH:23][CH:24]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2751588Tert-butyl 4-formylbenzoateHCID 4311764Sodium borohydrideHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

生成物 1

HCID 178450684HCID 178450684、化合物収率 93%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-20 °C

実験手順

A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 3 (70 mg, 287 μmol) and 4-formyl-benzoic acid mono tert-butyl ester (150 mg, 727 μmol) in MeOH (3 ml) was stirred at 45° C. for overnight to give a suspension, cooled to −20° C. and was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in EtOAc (5 ml) and washed with water (2×4 ml), dried over MgSO4 and concentrated in vacuo. Crystallization from EtOAc/hexanes afforded a white solid as desired product (116 mg, 93% yield). MS +m/z: 434 (M+H)+

後処理

  1. customto give a suspension
  2. filtrationwas filtered
  3. customto collect the solid
  4. customThe solvent was removed
  5. dissolutionthe reaction mixture was redissolved in EtOAc (5 ml)
  6. washwashed with water (2×4 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customCrystallization from EtOAc/hexanes

出典と根拠

ORDレコード
ord-1375f1f2a3ea4b22a7a1d48215690faa
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09428469B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート