Dicyclohexylcarbodiimide → HCID 178451273, compound

HRID 358557Notes

Reaction equation

HRID 358557 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 178451273HCID 178451273, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7a7633551c794599858e8b35d9ef8166
Source dataset
uspto-grants-1991_03
Patent number
US04997667

Reaction notes

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