Triethylamine → N'-(3-Bromophenyl)tetrahydro-2H-thiopyran-4-carbohydrazide

HRID 1619109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619109
C(Cl)(=O)C(Cl)=O.[S:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1.Cl.[Br:17][C:18]1[CH:19]=[C:20]([NH:24][NH2:25])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:24][NH:25][C:13]([CH:10]2[CH2:9][CH2:8][S:7][CH2:12][CH2:11]2)=[O:15])[CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 337573-Bromophenylhydrazine hydrochlorideHCID 65578Oxalyl chlorideHCID 21598642Tetrahydrothiopyran-4-carboxylic acid

Produkt 1

HCID 66958508N'-(3-Bromophenyl)tetrahydro-2H-thiopyran-4-carbohydrazideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (1.20 mL, 14.2 mmol) was added dropwise to a stirred solution of tetrahydro-2H-thiopyran-4-carboxylic acid (WO2007006732, 2.00 g, 13.7 mmol) in dichloromethane (25 mL). Then, two drops of N,N′-dimethylformamide were added and stirring was continued. After 1.5 hours, the resultant solution was added dropwise over 30 minutes to a stirred, cooled (ice-bath) solution of (3-bromophenyl)hydrazine hydrochloride (3.05 g, 13.7 mmol) and triethylamine (4.20 mL, 30.1 mmol) in dichloromethane (40 mL). After the addition, the mixture was warmed to room temperature and stirred for two hours. The mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and the solid was filtered and dried to give the title compound (2.57 g, 60%) as an off-white solid.

Aufarbeitung

  1. additionAfter the addition
  2. stirringstirred for two hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with 4% aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was triturated with diethyl ether
  9. filtrationthe solid was filtered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0e8cfd6102fa4244b5597544d3bc83be
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772288B2

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