Diisopropylcarbodiimide → HCID 178524175, compound

HRID 1406490Notes

Reaction equation

HRID 1406490 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=S.C([O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)C.CC(C)N=C=NC(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:19]2[CH:20]=[CH:21][C:16]([C:15]([OH:24])=[O:14])=[CH:17][C:18]=2[N:23]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 178524175HCID 178524175, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3-dichloro-2-isothiocyanato-benzene (5.66 g, 27.8 mmol) and 3,4-diamino-benzoic acid ethyl ester (5.00 g, 27.8 mmol) in 40 mL DMF was stirred for 2 h. DIC (4.40 mL, 28.2 mmol) was added and stirred overnight at ambient temperature. The mixture was stirred for 30 min at 80° C., diluted with water and concentrated i.vac. The residue was taken up in ethanol and 60 mL 1 M aq. NaOH was added and stirred overnight at reflux. Ethanol was evaporated and the aq. phase was filtered. The filtrate was acidified with formic acid, cooled, filtered and dried.

Workup

  1. stirringstirred overnight at ambient temperature
  2. stirringThe mixture was stirred for 30 min at 80° C.
  3. concentrationconcentrated i.vac
  4. addition60 mL 1 M aq. NaOH was added
  5. stirringstirred overnight
  6. temperatureat reflux
  7. customEthanol was evaporated
  8. filtrationthe aq. phase was filtered
  9. temperaturecooled
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-2c5d7b5de6b04b06bc0c29361772753b
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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