Dicyclohexylcarbodiimide → HCID 54544075, compound

HRID 2351301Notes

Reaction equation

HRID 2351301 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:12][C:13](O)=[O:14].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:11]1[S:10][C:2]2=[N:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]2[C:13](=[O:14])[CH2:12]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 19846120HCID 19846120, compound

Product 1

HCID 54544075HCID 54544075, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(2-Benzimidazolylthio)-3-(2-pyridyl)propionic acid (3.7 g) was suspended in dichloromethane (100 ml) and was cooled to 0° C. N,N'-Dicyclohexylcarbodiimide (2.55 g) was added and the mixture was left to stir until t.l.c. showed no starting material. The solvent was removed under reduced pressure and the residue suspended in acetone and filtered. The solvent was removed under reduced pressure and the residue was dissolved in chloroform. The organic solution was washed with dilute sodium hydrogen carbonate solution then water and was dried (MgSO4). The residue was purified on silica using chloroform as eluent to give 2,3 dihydro-2-(2-pyridyl)-[1,3]-thiazino[3,2-a]benzimidazol-4-one 1/4 hydrate (1.8 g,) mp 165.5°-167.5° C. decomp.

Workup

  1. waitthe mixture was left
  2. customThe solvent was removed under reduced pressure
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in chloroform
  6. washThe organic solution was washed with dilute sodium hydrogen carbonate solution
  7. dry with materialwater and was dried (MgSO4)
  8. customThe residue was purified on silica

Sources & evidence

ORD record
ord-b2705084b29f4301bdeaea08010bc051
Source dataset
uspto-grants-1989_10
Patent number
US04873237

Reaction notes

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