Sulfuryl chloride → 3-[(4-Chlorophenyl)sulfanyl]-2,5-dimethyl-1H-indole-4-carbonitrile

HRID 2240551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240551
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([CH3:12])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.C[N:19](C)[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2N(C)C)[CH:23]=CC=1.[NH2:34]C1C=CC(Cl)=C(C=1)C#N>ClCCl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:28]3[C:29]([C:20]#[N:19])=[C:24]([CH3:23])[CH:25]=[CH:26][C:27]=3[NH:34][C:10]=2[CH3:12])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 24648Sulfuryl chlorideHCID 88675Proton spongeHCID 3217461-[(4-Chlorophenyl)sulfanyl]propan-2-oneHCID 109972345-Amino-2-chlorobenzonitrile

Produkt 1

HCID 210778313-[(4-Chlorophenyl)sulfanyl]-2,5-dimethyl-1H-indole-4-carbonitrileAusbeute 12,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A stirred solution of 1-[(4-chlorophenyl)thio]-acetone (6.14 g) in dry dichloromethane (150 ml) at −78° C. was treated with sulphuryl chloride (2.25 ml). After 30 min a prepared solution of N,N,N′,N′-tetramethyl-1,8-naphthalenediamine (6.01 g) and 5-amino-2-chloro-benzonitrile (3.89 g) in dry dicholoromethane (80 ml) was added dropwise over 30 min. The mixture was stirred for a further 2 h, after which triethylamine (4.26 ml) was added and the reaction allowed to reach room temperature. The reaction mixture was diluted with dichloromethane (200 ml), washed with water, 1N HCl and brine. The organic phase was dried (MgSO4), evaporated in vacuo, and the residue purified by flash column chromatography eluting with isohexane and ethyl acetate (1:1) to give the sub-title compound (1 g), and the regioisomer (600 mg) used in example 6 below.

Aufarbeitung

  1. customto reach room temperature
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated in vacuo
  5. customthe residue purified by flash column chromatography
  6. washeluting with isohexane and ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-54ed0134b48c427a9a2e6034bc8f55ea
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723373B2

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