Acetic Acid → HCID 178512757, compound

HRID 1434692Notes

Reaction equation

HRID 1434692 reaction equation
C(O[C:4](=[NH:20])[C:5]1[CH:10]=[CH:9][C:8]([S:11](=[O:19])(=[O:18])[NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)C.[NH2:21][NH2:22].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH:27]=O.C(O)(=O)C>C(O)C>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[NH:12][S:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]([NH:21][N:22]=[CH:27][C:26]2[CH:29]=[CH:30][C:31]([Cl:32])=[C:24]([Cl:23])[CH:25]=2)=[NH:20])=[CH:10][CH:9]=1)(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 227103,4-DichlorobenzaldehydeHCID 86611695HCID 86611695, compound

Product 1

HCID 178512757HCID 178512757, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(thiazol-2-ylsulfamoyl)-benzimidic acid ethyl ester (0.965 mmol) and hydrazine (0.5 mL) was stirred for 10 min. in ethanol (5 mL) at room temperature. The solution was concentrated in vacuo and DMF (5 mL) was added followed by the addition of 3,4-dichloro-benzaldehyde (1.06 mmol). Acetic acid (1 mL) was added and the solution was stirred for 2 h at room temperature. The solution was quenched with sat NaHCO3, extracted with ethyl acetate, washed with brine and dried with MgSO4. The reaction was concentrated in vacuo and that material was purification by column chromatography to yield 4-(thiazol-2-ylsulfamoyl)-N-(3,4-Dichloro-benzylideneamino)-benzamidine (0.39 mmol).

Workup

  1. concentrationThe solution was concentrated in vacuo and DMF (5 mL)
  2. additionwas added
  3. customThe solution was quenched with sat NaHCO3
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. concentrationThe reaction was concentrated in vacuo
  8. custompurification by column chromatography

Sources & evidence

ORD record
ord-19f6af1c3ef2461096e346576818a48b
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

Loading…