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

HRID 1374789ノート

反応式

HRID 1374789 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 210778313-[(4-Chlorophenyl)sulfanyl]-2,5-dimethyl-1H-indole-4-carbonitrile収率 12.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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 hours, 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 iso-hexane and ethyl acetate (1:1) to give the sub-title compound (1 g).

後処理

  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 iso-hexane and ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-2b475827cac04725ba163751e70b56ef
出典データセット
uspto-grants-2007_01
特許番号
US07166607B2

反応ノート

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