Water → 4-(ethylthio)-2-methyl-1H-imidazole-5-methanol

HRID 36017Notes

Reaction equation

HRID 36017 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([S:13][C:14]1[N:15]=[C:16]([CH3:24])[NH:17][C:18]=1[C:19](OCC)=[O:20])[CH3:12].C(Cl)(=O)C.O>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:11]([S:13][C:14]1[N:15]=[C:16]([CH3:24])[NH:17][C:18]=1[CH2:19][OH:20])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 10130590ethyl 4-(ethylthio)-2-methyl-1H-imidazole-5-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 214790114-(ethylthio)-2-methyl-1H-imidazole-5-methanolYield 76.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

11.64 cm3 of a 1.2M solution of diisobutylaluminium hydride in toluene is added over 10 minutes at -70° C. to a solution of 1 g of ethyl 4-(ethylthio)-2-methyl-1H-imidazole-5-carboxylate (obtained as in Preparation 1 using, in Stage B, acetyl chloride instead of pentanoyl chloride) in 100 cm3 of methylene chloride. The mixture is agitated for 3 hours at ambient temperature then hydrolyzed by the addition of 1 cm3 of water. After agitation for 15 minutes, then filtering, the insoluble part is washed with 20 cm3 of methylene chloride then 5 times with 20 cm3 of a methylene chloride--methanol mixture (9-1). After drying, the filtrate is brought to dryness under reduced pressure. The residue (760 mg) is impasted in 7.6 cm3 of methylene chloride and 614 mg of the expected product is obtained. M.p.=153° C. IR Spectrum: Absence >C=O Absorption OH/NH complex region Heteroaromatic 1582 cm-1 -1524 cm-1

Workup

  1. customobtained as in Preparation 1 using
  2. waitAfter agitation for 15 minutes
  3. filtrationfiltering
  4. washthe insoluble part is washed with 20 cm3 of methylene chloride
  5. customAfter drying

Sources & evidence

ORD record
ord-491467a9de264eb1927f75ff0f8550d4
Source dataset
uspto-grants-1995_05
Patent number
US05412101

Reaction notes

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