Water → HCID 178489010, compound

HRID 1587407Notes

Reaction equation

HRID 1587407 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)Cl)=[CH:5][CH:4]=1.[NH2:21][C:22]([NH2:27])=[N:23][C:24]([NH2:26])=[S:25].O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:26]=[C:24]([NH:23][C:22]([NH2:27])=[NH:21])[S:25][C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724563AmidinothioureaHCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-one

Product 1

HCID 178489010HCID 178489010, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (1.00 g) and N-diaminomethylenethiourea (0.65 g) in ethanol (20 ml) was refluxed for 12 hours. After allowing to cool to ambient temperature, then the reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed n alumina, eluting with a mixture of chloroform and methanol. The desired fractions were combined and concentrated in vacuo. The residue was washed with isopropy ether to give 4,5-bis(4methoxyphenyl)-2-guanidinothiazole (0.65 g).

Workup

  1. temperaturewas refluxed for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed n alumina
  7. washeluting with a mixture of chloroform and methanol
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with isopropy ether

Sources & evidence

ORD record
ord-d09103a12bc443c9b1552e7355d49de0
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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