Ammonium Hydroxide → (E)-3-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenamide

HRID 2081876Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:7](/[CH:10]=[C:11](\[CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)/[C:12]([OH:14])=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[OH-].[NH4+:34]>>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:7](/[CH:10]=[C:11](\[CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)/[C:12]([NH2:34])=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 14923Ammonium Hydroxide

HCID 24386Thionyl Chloride

HCID 100474443-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-thiophen-2-ylmethyl-acrylic acid

Product 1

HCID 70041851(E)-3-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenamide

Procedure

(E)-3-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid, prepared in Example 1, was treated with thionyl chloride and then ammonium hydroxide, as described in Example 54, to give the title compound; mp 184°-185° C.

Sources & evidence

ORD record: ord-f9b3bf62928e4fca918a1c1e51fac566
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05185351

Reaction notes

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