Tetrahydrofuran → Benzimidazol-2-one

HRID 2250360Notes

Reaction equation

HRID 2250360 reaction equation
[C:1]([N:8]1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].O1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[N:3]1[C:1](=[O:2])[N:8]=[C:14]2[CH:15]=[CH:16][CH:17]=[CH:6][C:7]=12

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 162542Benzimidazol-2-one

Procedure

In Scheme I, 2-fluoro-nitrobenzene is reacted with a primary amine, intermediate (h), wherein R1 is as described herein, to provide intermediate (i), which is reduced to a diaminophenyl, intermediate (j). The diaminophenyl is reacted with carbonyldiimidazole in the presence of an inert diluent, such as tetrahydrofuran, at a temperature range of from about 20° C. to about 40° C. for between about 12 and about 30 hours, to provide a benzoimidazolone compound of intermediate (d). A representative synthesis of a compound of intermediate (d) is described herein in Example 1, steps (a)-(c).

Workup

  1. waitat a temperature range of from about 20° C. to about 40° C. for between about 12 and about 30 hours

Sources & evidence

ORD record
ord-dc8fc0e5417846e289c211c17c932749
Source dataset
uspto-grants-2008_01
Patent number
US07317022B2

Reaction notes

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