Benzaldehyde → 4-Benzylidene-2-sulfanyl-4H-imidazol-5-ol

HRID 2075298Notes

Reaction equation

HRID 2075298 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.Cl>O>[CH:8](=[C:7]1[NH:1][C:2](=[S:3])[NH:4][C:5]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12740302-Thiohydantoin

Product 1

HCID 28316104-Benzylidene-2-sulfanyl-4H-imidazol-5-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask equipped with a magnetic stirrer, nitrogen pressure, and reflux condenser was charged with thiohydantoin (24.9 g, 0.215 mol), benzaldehyde (22.8 g, 0.215 mol), triethylamine (43 g, 0.43 mol), and water (250 mL). Slight warming and vigorous stirring brought everything into solution. The mixture was stirred overnight and then transferred to an Erlenmeyer flask equipped with a magnetic stirrer. The pH was brought to ca. 3 with 3 M hydrochloric acid, and the mixture was stirred for 3 hr. The resulting solid was collected and washed with water and 2×50 mL of diethyl ether. The product weighed 97.6 g (97%). No other components were found in an HPLC trace at 260 and 350 nm. NMR (d6-DMSO) δ 7.2-7.8 (m, 5H), 6.4 (s, 1H), 3.5 (bs, 2H).

Workup

  1. customA flask equipped with a magnetic stirrer
  2. temperaturenitrogen pressure, and reflux condenser
  3. temperatureSlight warming
  4. stirringThe mixture was stirred overnight
  5. customequipped with a magnetic stirrer
  6. stirringthe mixture was stirred for 3 hr
  7. customThe resulting solid was collected
  8. washwashed with water and 2×50 mL of diethyl ether

Sources & evidence

ORD record
ord-184c56019cd5419189be9f310614b623
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

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