Dicyclohexylcarbodiimide → HCID 178451273、化合物

HRID 358557ノート

反応式

HRID 358557 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(N)=S)=[CH:4][N:3]=1.[C:12]([O:16][C:17](=[O:20])[CH2:18][NH2:19])([CH3:15])([CH3:14])[CH3:13].[CH:21]1([N:27]=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[C:7]([C:21](=[NH:27])[NH:19][CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:20])=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 151417Glycine tert-butyl esterHCID 47003394N-(6-Chloropyridin-3-yl)thiourea

生成物 1

HCID 178451273HCID 178451273、化合物収率 36%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1.2 g (6.4 mmol) of 2-chloro-5pyridylthiourea, 1 g (7.68 mmol) of glycine tert-butyl ester and 1.45 g (7.04 mmol) of dicyclohexylcarbodiimide in 30 ml of ethyl acetate is heated for 2.5 hr at 60° C. The dicyclohexylthiourea precipitate formed is eliminated by filtration. The filtrate is concentrated to dryness The product obtained is taken up in 20 ml of dichloromethane and then extracted with a 0.25 N aqueous hydrochloric acid solution (4 × 30 ml). The acid solution is then neutralized with a 1 N sodium hydroxide solution, and thereafter is extracted with dichloromethane (3× 20 ml), thus permitting 0.65 g (yield 36%) of tert-butyl N-[2-chloro-5-aminopyridyl(imino)methyl]-2-aminoethanoate to be obtained in the form of an oil.

後処理

  1. customThe dicyclohexylthiourea precipitate
  2. customformed
  3. filtrationis eliminated by filtration
  4. concentrationThe filtrate is concentrated to dryness The product
  5. customobtained
  6. extractionextracted with a 0.25 N aqueous hydrochloric acid solution (4 × 30 ml)
  7. extractionis extracted with dichloromethane (3× 20 ml)

出典と根拠

ORDレコード
ord-7a7633551c794599858e8b35d9ef8166
出典データセット
uspto-grants-1991_03
特許番号
US04997667

反応ノート

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