Formic Acid → [Benzenesulfonyl-(4-cyano-2-methylsulfanyl-phenyl)-methyl]-carbamic acid tert-butyl ester

HRID 59642

Reaktionsgleichung

Reaktionsgleichung von HRID 59642
C(O)=O.[C:4](=[O:11])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:5].[CH:12]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[S:22][CH3:23])=O.[C:24]1([S:30]([O-:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+]>C1COCC1.O>[C:7]([O:6][C:4](=[O:11])[NH:5][CH:12]([S:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:32])=[O:31])[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[S:22][CH3:23])([CH3:10])([CH3:9])[CH3:8]

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium saltHCID 581337424-Formyl-3-(methylsulfanyl)benzonitrile2×

Produkt 1

HCID 118692905[Benzenesulfonyl-(4-cyano-2-methylsulfanyl-phenyl)-methyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Formic acid (3.0 mL, 79 mmol) is added to a solution of tert-butyl carbamate (1.436 g, 12.3 mmol), 4-formyl-3-methylsulfanyl-benzonitrile (INTERMEDIATE 1; 1.975 g, 11.1 mmol) and sodium benzenesulfinate (2.012 g, 12.2 mmol) in a mixture of THF (3.0 mL) and water (7 mL), and the mixture is stirred at room temperature for 3 days. Water is added, the precipitate is filtered off and washed with water. The precipitate is treated with tert-butyl methyl ether, and the mixture is stirred for 30 min. The precipitate is filtered off, washed with tert-butyl methyl ether and dried. Yield: 3.5 g.

Aufarbeitung

  1. filtrationthe precipitate is filtered off
  2. washwashed with water
  3. additionThe precipitate is treated with tert-butyl methyl ether
  4. stirringthe mixture is stirred for 30 min
  5. filtrationThe precipitate is filtered off
  6. washwashed with tert-butyl methyl ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-69decbb807f24d3d9db94a2635fc07e2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440930B2

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