Carbamate → 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethyl 3,5-dichlorobenzoylcarbamate

HRID 1005551Notes

Reaction equation

HRID 1005551 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.C(=O)([O-])N.[Cl:26][C:27]1[CH:28]=[C:29]([CH:35]=[C:36]([Cl:38])[CH:37]=1)[C:30]([N:32]=[C:33]=[O:34])=[O:31]>>[Cl:26][C:27]1[CH:28]=[C:29]([CH:35]=[C:36]([Cl:38])[CH:37]=1)[C:30]([NH:32][C:33](=[O:34])[O:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:9])[CH3:10])[N:7]=1)=[O:31]

Participants

4

Reactant 3

HCID 276CarbamateHCID 473933(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanolHCID 135133493,5-Dichlorobenzoyl isocyanate

Product 1

HCID 4781915-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethyl 3,5-dichlorobenzoylcarbamateYield 78%

Procedure

The compound 19 (300 mg, 0.869 mmol) was converted to the carbamate with 3,5-dichlorobenzoyl isocyanate (1.5 eq.) in the same manner as the example 66 to give the compound 87 (380 mg, 78%) as crystals. Mp.124-125° C. Rf 0.23 (1:2 EtOAc-hexane)

Sources & evidence

ORD record
ord-c94c5db179054fd083e5aa12ed35038c
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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