Ammonia → 1-(4-Amino-3-methylphenyl)-5-iodo-2,4-dimethylimidazole

HRID 649544Notes

Reaction equation

[I:1]I.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]2[CH3:16])=[CH:6][C:5]=1[CH3:17].N.CCOCC>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([I:1])=[C:13]([CH3:15])[N:12]=[C:11]2[CH3:16])=[CH:6][C:5]=1[CH3:17]

Participants

Conditions

Temperature: 55 °C

Procedure

Silver sulphate (21.8 g) and crushed iodine (35.5 g) were added portionwise to a stirred solution of 1-(4-amino-3-methylphenyl)-2,4-dimethylimidazole (25.4 g) in sulphuric acid (100 cm3) cooled to -10°. After heating at 55° C. for 2 hours, the cooled mixture was poured onto ice (500 g). The mixture was cautiously adjusted to pH8 by addition of concentrated ammonia solution (S.G. 0.880) and extracted with chloroform (2×500 cm3). The organic extracts were combined, filtered through "Arbocel" (silica) [Trade Mark], and washed with saturated sodium thiosulphate solution (200 cm3). The organic solution was dried (MgSO4) and evaporated in vacuo to give a residue which, on trituration with ether, gave the title compound (32.25 g) as a crude solid which was used without further purification in Preparation 22.

Workup

temperaturecooled to -10°
additionthe cooled mixture was poured onto ice (500 g)
extractionextracted with chloroform (2×500 cm3)
filtrationfiltered through "Arbocel" (silica) [Trade Mark]
washwashed with saturated sodium thiosulphate solution (200 cm3)
dry with materialThe organic solution was dried (MgSO4)
customevaporated in vacuo
customto give a residue which

Sources & evidence

ORD record: ord-8401083141de4ad28735b63fcf3ceeee
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04740513

Reaction notes

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