Water → HCID 67229872, compound

HRID 1406473Notes

Reaction equation

HRID 1406473 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.CC(C)N=C=NC(C)C.O>CN(C=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[NH:22][C:23]1[NH:12][C:7]2[CH:6]=[C:5]([C:4]([OH:3])=[O:13])[CH:10]=[CH:9][C:8]=2[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12734DiisopropylcarbodiimideHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 67229872HCID 67229872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,4-diamino-benzoic acid ethyl ester (5.0 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. DIC (4.40 mL, 28.2 mmol) was added and the mixture stirred overnight. After 30 min stirring at 80° C. water was added and the mixture was concentrated i.vac. The residue was taken up in ethanol and 1 M aq. NaOH. The mixture stirred overnight at reflux. Ethanol was evaporated and the aq. phase diluted with water. The precipitate was filtered and washed with water. The filtrate was acidified with formic acid and cooled. The mixture was filtered and washed with water.

Workup

  1. stirringthe mixture stirred overnight
  2. additionwas added
  3. concentrationthe mixture was concentrated i.vac
  4. stirringThe mixture stirred overnight
  5. temperatureat reflux
  6. customEthanol was evaporated
  7. additionthe aq. phase diluted with water
  8. filtrationThe precipitate was filtered
  9. washwashed with water
  10. temperaturecooled
  11. filtrationThe mixture was filtered
  12. washwashed with water

Sources & evidence

ORD record
ord-93bd9a02f31f46cfb12a7d1ca58b4c51
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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