3-(p-Methoxyphenyl)-5-phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione → Phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione

HRID 1974575Notes

Reaction equation

HRID 1974575 reaction equation
COC1C=CC([N:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11](O)[C:10]2=[S:21])=CC=1.C(=S)([O-:24])N>C(Cl)Cl>[C:14]1([C:12]2[NH:11][C:10](=[S:21])[N:9]([OH:24])[CH:13]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 149385613-(p-Methoxyphenyl)-5-phenyl-1-hydroxy-1,2-dihydroimidazole-2-thioneHCID 178514129HCID 178514129, compound

Product 1

HCID 24783967Phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The thiohydroxamine acid, 3-(p-methoxyphenyl)-5-phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione, was prepared from the thiocarbamate in a manner similar to that used in Example I. The 3-(p-methoxyphenyl)-5-phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione was recrystallized from methylene chloride/hexane to give white crystalline material. mp: 168° C. (dec); IR (CH2Cl2): 2800-1756-1510-1383-1361-1241-1133 cm-1 ; 1H NMR (200 MHz, CDCl3 : DMSO 1:1): 3.82 (3H, OCH3, s); 6.5 (2H, d); 7.15 (1H, CH=, s); 7.4 (3H, m); 7.54 (2H, d); 7.71 (2H, d); 11.85 (1H, OH, br); 13C NMR (CDCl3 : DMSO 1:1): 54 (OCH3): 110.6 (CH=); 112.6 (CH); 125.6 (CH); 125.7 (CH); 127 (CH); 127.2 (CH); 129.5 (Cq); 157.6 (CH); Anal. Calcd for C16H14N2O2 5: C, 64.40; H, 4.73; N, 9.39; S,10.74 Found C, 64.48; H, 4.24; N,9.43; S, 10.68.

Workup

  1. customThe 3-(p-methoxyphenyl)-5-phenyl-1-hydroxy-1,2-dihydroimidazole-2-thione was recrystallized from methylene chloride/hexane
  2. customto give white crystalline material

Sources & evidence

ORD record
ord-bb4e99782d974f15be6b3c40c85d01c4
Source dataset
uspto-grants-1994_02
Patent number
US05283271

Reaction notes

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