Triethylamine → HCID 178524175, compound

HRID 1406437Notes

Reaction equation

HRID 1406437 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.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.CN(C)C1C=CN=CC=1>[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

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 178524175HCID 178524175, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent4×

Procedure

To 3,4-diamino-benzoic acid ethyl ester (4.0 g, 22.2 mmol) in 100 mL dichloromethane was added 1,3-dichloro-2-isothiocyanato-benzene (4.5 g, 22 mmol) in 50 mL dichloromethane. After stirring overnight and refluxing for another 6 hrs, the solvent was evaporated. After adding 200 mL dichloromethane, triethylamine (7 mL, 50 mmol) and 4-dimethylaminopyridine (100 mg, 0.82 mmol) have been added, methanesulfonyl chloride (1.7 mL, 22 mmol) in 50 mL dichloromethane was added to the reaction mixture. After stirring for 2 h, another portion of methanesulfonyl chloride (1.7 mL, 22 mmol) was added. After stirring at room temperature overnight, the solvent was evaporated. The residue was mixed with 150 mL methanol and 40 mL 4N NaOH (aq), stirred over night, another 20 mL 4N NaOH (aq) added and refluxed for 2 h. The solvent was removed, the residue mixed with water and methanol and the mixture neutralized with 4 N HCl (aq). The mixture was filtered, washed with water and dried.

Workup

  1. temperaturerefluxing for another 6 hrs
  2. customthe solvent was evaporated
  3. additionhave been added
  4. stirringAfter stirring for 2 h
  5. stirringAfter stirring at room temperature overnight
  6. customthe solvent was evaporated
  7. additionThe residue was mixed with 150 mL methanol and 40 mL 4N NaOH (aq)
  8. stirringstirred over night
  9. additionanother 20 mL 4N NaOH (aq) added
  10. temperaturerefluxed for 2 h
  11. customThe solvent was removed
  12. additionthe residue mixed with water and methanol
  13. filtrationThe mixture was filtered
  14. washwashed with water
  15. customdried

Sources & evidence

ORD record
ord-6fb501561b064a4eaa187d62daa87b5a
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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