5-(1-Hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole → 5-Acetyl-1-methyl-4-(phenylmethyl)thioimidazole

HRID 373683Notes

Reaction equation

HRID 373683 reaction equation
[OH:1][CH:2]([C:4]1[N:8]([CH3:9])[CH:7]=[N:6][C:5]=1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:3]>CC(C)=O.[Mn]>[C:2]([C:4]1[N:8]([CH3:9])[CH:7]=[N:6][C:5]=1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 198109685-(1-Hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole

Product 1

HCID 198109645-Acetyl-1-methyl-4-(phenylmethyl)thioimidazoleYield 21.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 23930ManganeseSolvent

Procedure

5-(1-Hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole (6.2 g. 25 mmol) in acetone (310 ml) and active manganese IV oxide (62 g), under a calcium chloride drying tube, were mechanically stirred and refluxed for 4 hours. The reaction mixture was cooled, filtered, washed with dichloromethane and evaporated under reduced pressure to provide crude product. Purification by flash chromatography starting with dichloromethane followed by 1%, 2% and 10% methanol in dichloromethane provided 1.3 g of 5-acetyl-1-methyl-4-(phenylmethyl)thioimidazole (21%) and 3.6 g of starting material 5-(1-hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole (58%). The yield based on the starting material consumed is 50%; mp 62° C.; -H NMR(300 MHz, CDCl3) δ 2.49 (s, 3H, CH3CO), 3.86 (s, 3H, NCH3), 4.45 (3, 2H, SCH2), 7.26-7.37 (m, 5H, ArH), 7.49(s, 1H, 1m H-2); 13C NMR(75 MHz, CDCl3) δ 30.4, 35.6, 37.2, 127.2, 128.1, 128.5, 129.0, 137.8, 142.0, 145.4, 188.4 (C=O) ppm; IR (CCl14) 3060, 2960, 1665 (C=O), 1550, 1515, 1250, 825, 730 cm-1, LRMS (ei) m/z 246 (M+ -SH, 100), 155 (23), 91 (C7H7+ 95), 81 (29), 42 (23); HRMS (ei) calc. 246.0827 obsd. 246.0826.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washwashed with dichloromethane
  5. customevaporated under reduced pressure
  6. customto provide crude product
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-5a4a4f37dc3841d48e6f6e11d07190f9
Source dataset
uspto-grants-1992_11
Patent number
US05164511

Reaction notes

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