Hydrochloric Acid → HCID 178493103, compound

HRID 1855410Notes

Reaction equation

HRID 1855410 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=S)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.IC.[C:21]1([CH2:27][C:28]([NH:30][NH2:31])=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].Cl>CC(C)=O.C(OCC)C>[CH2:27]([C:28]1[NH:18][C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:31][N:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 70301Benzeneacetic acid, hydrazideHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 178493103HCID 178493103, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A solution of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (400 mg, 1.52 mmol) in acetone (25 ml) was treated with iodomethane (0.14 ml, 2.29 mmol) and stirred at 20° C. for 16 h. The reaction mixture was concentrated and the crude S-methyl-isothiourea redissolved in ethanol (25 ml). Phenylacetic acid hydrazide (252 mg, 1.52 mmol) was added and the mixture was refluxed for 16 h under argon. After cooling to 20° C., 2 N sodium hydroxide solution (5 ml) was added and the mixture was refluxed for 2 h. After cooling to 20° C., the mixture was brought to pH 7 by careful addition of 1 N aqueous hydrochloric acid and then extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporation under reduced pressure to afford a sticky semisolid which was triturared in diethyl ether (3 mL). Filtration yielded the title compound (146 mg, 27%) as greyish solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe crude S-methyl-isothiourea redissolved in ethanol (25 ml)
  3. temperaturethe mixture was refluxed for 16 h under argon
  4. temperatureAfter cooling to 20° C.
  5. temperaturethe mixture was refluxed for 2 h
  6. temperatureAfter cooling to 20° C.
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over sodium sulfate and evaporation under reduced pressure
  9. customto afford a sticky semisolid which
  10. filtrationFiltration

Sources & evidence

ORD record
ord-bfc1f334ab2c41a6aba19fd5a57aab89
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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