Pyridine → 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarbonitrile

HRID 397654ノート

反応式

HRID 397654 の反応式
C(Cl)(=O)C(Cl)=O.CN(C)C=O.N1C=CC=CC=1.[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[S:27]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[C:36]([NH2:38])=O)(=[O:29])=[O:28]>C(#N)C>[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[S:27]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[C:36]#[N:38])(=[O:28])=[O:29]

参加物

6

反応物 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 230006771H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide

生成物 1

HCID 230007671-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarbonitrile収率 35.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Oxalyl chloride (5.00 ml) was added dropwise to a solution of dimethylformamide (4.43 ml) in acetonitrile (200 ml) at 0° C. The mixture was stirred for 20 mins. and a suspension of pyridine (9.66 ml) and 1-(1H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide (14.73 g) [see Preparation 17] in acetonitrile (100 ml) was added over a period of 10 mins. The reaction mixture was stirred for a further 20 mins. after which time the solvent was removed under reduced pressure. The residue was diluted with diethyl ether and washed with water, brine, dried over magnesium sulphate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 70:30, by volume, hexane:ethyl acetate to afford 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarbonitrile (4.9 g).

後処理

  1. stirringThe reaction mixture was stirred for a further 20 mins
  2. customafter which time the solvent was removed under reduced pressure
  3. additionThe residue was diluted with diethyl ether
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel eluting with 70:30, by volume, hexane

出典と根拠

ORDレコード
ord-a585ffcd2f7f4e3a866bb87421b2e9e2
出典データセット
uspto-grants-2003_08
特許番号
US06610707B1

反応ノート

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