Dicyclohexylcarbodiimide → HCID 178524175, compound

HRID 1406442Notes

Reaction equation

HRID 1406442 reaction equation
C([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH2:12])[CH:6]=1)C.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[N:22]=[C:23]=S.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[NH:22][C:23]1[NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:3])=[O:13])=[CH:6][C:7]=2[N:12]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 178524175HCID 178524175, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,4-diamino-benzoic acid ethyl ester (5.00 g, 27.8 mmol) and 1,3-dichloro-2-isothiocyanato-benzene (5.66 g, 27.8 mmol) in 40 mL DMF was stirred for 2 h under argon. DCC (5.72 g, 27.8 mmol) was added and mixture heated to 80° C. for 45 min. After stirring the mixture was diluted with water and concentrated i.vac. The residue was diluted with ethanol and 1 M NaOH (aq). The mixture was heated to 100° C. and stirred overnight. Then ethanol was evaporated and the aq. phase was cooled, acidified with acetic acid, filtered and the solid washed with water.

Workup

  1. stirringAfter stirring the mixture
  2. concentrationconcentrated i.vac
  3. additionThe residue was diluted with ethanol and 1 M NaOH (aq)
  4. temperatureThe mixture was heated to 100° C.
  5. stirringstirred overnight
  6. customThen ethanol was evaporated
  7. temperaturethe aq. phase was cooled
  8. filtrationfiltered
  9. washthe solid washed with water

Sources & evidence

ORD record
ord-ae4e5aa82381448b8da1ec23f2ca8e01
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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