Formic Acid → Tert-butyl N-[(Benzenesulfonyl)(2-bromo-4-cyanophenyl)methyl]carbamate

HRID 59651

反応式

HRID 59651 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[Na+].[C:13]1([S:19]([O-:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([NH:26][C:27](=[O:29])[O-:28])(C)(C)C.[CH:30](O)=O.[CH2:33]1[CH2:37]OC[CH2:34]1>O>[C:33]([O:28][C:27](=[O:29])[NH:26][CH:10]([S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20])[C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Br:1])([CH3:34])([CH3:37])[CH3:30]

参加物

7

反応物 5

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 2723840Benzenesulfinic acid, sodium saltHCID 205105183-Bromo-4-formylbenzonitrileHCID 21252905Tert-butylcarbamate

生成物 1

HCID 118691238Tert-butyl N-[(Benzenesulfonyl)(2-bromo-4-cyanophenyl)methyl]carbamate

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

3-Bromo-4-formyl-benzonitrile (20.5 g, 97.7 mmol), benzenesulfinic acid sodium salt (16.03 g, 97.6 mmol) and tert-butylcarbamate (11.4 g, 97.7 mmol) are suspended in water (312 mL) and THF (78 mL). Formic acid (28.8 g, 625 mmol) is added and the solution is stirred at room temperature for 6 days. Water (300 mL) is added and the precipitate is filtered off, washed with water and dried. The crude product is further purified by precipitation from tert-butylmethylether. Yield: 26.8 g; ESI mass spectrum: [M+Na]+=473 (bromine isotope pattern).

後処理

  1. filtrationthe precipitate is filtered off
  2. washwashed with water
  3. customdried
  4. customThe crude product is further purified by precipitation from tert-butylmethylether

出典と根拠

ORDレコード
ord-3e802816fb3946918173d636cb788fa2
出典データセット
uspto-grants-2016_09
特許番号
US09440930B2

関連ノート

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