1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-, carbamate (ester) → 1H-Imidazole-2-acetonitrile, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-

HRID 1857766Notes

Reaction equation

HRID 1857766 reaction equation
C(O[CH2:5][CH2:6][C:7]1[N:8]([CH2:24]C2C=CC=CC=2[N+]([O-])=O)[C:9]([S:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[C:10]([CH:12]([CH3:14])[CH3:13])[N:11]=1)(=O)N.ClC1C=C(SC2N(CC3C=CC=CC=3[N+]([O-])=O)C(CCO)=[N:45]C=2C(C)C)C=C(Cl)C=1.C(OCCC1N(CC2C=CC([N+]([O-])=O)=CC=2)C(SC2C=C(Cl)C=C(Cl)C=2)=C(C(C)C)N=1)(=O)N>>[Cl:23][C:18]1[CH:17]=[C:16]([S:15][C:9]2[N:8]([CH3:24])[C:7]([CH2:6][C:5]#[N:45])=[N:11][C:10]=2[CH:12]([CH3:14])[CH3:13])[CH:21]=[C:20]([Cl:22])[CH:19]=1

Participants

4

Reactant 3

HCID 4740691H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-, carbamate (ester)HCID 4740741H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-nitrophenyl)methyl)-HCID 4740761H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-nitrophenyl)methyl)-, carbamate (ester)

Product 1

HCID 4740091H-Imidazole-2-acetonitrile, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-Yield 87%

Procedure

2-(2-Carbamoyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(o-nitrobenzyl)-1H-imidazole (128c) was obtained from (126c) by the same synthetic process as that for (128a) in Example 140 (yield 87%). mp 163-165° C.

Sources & evidence

ORD record
ord-32f74dc550dc4297a11e87ce91d0b380
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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