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

HRID 59651

Reaktionsgleichung

Reaktionsgleichung von HRID 59651
[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]

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3e802816fb3946918173d636cb788fa2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440930B2

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