Phenol → Benzimidazole

HRID 1658581Notes

Reaction equation

HRID 1658581 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(O)=CC=C(C)C=1.ClC1C=CC=CC=1O.ClC1C=C(O)C=CC=1.FC(F)(F)C1C=C(O)C=CC=1.C1C(O)=CC=C(Br)C=1.FC1C=CC(O)=CC=1.FC1C=C(O)C=CC=1.C(C1C=CC(O)=CC=1)(=O)C.C(C1C=CC(O)=CC=1)#N.COC1C=CC(O)=CC=1.C(OC([NH:100][C:101](=[N:104]C(OCC)=O)SC)=O)C.C(OC(NC(=NC(OCCC)=O)SC)=O)CC.C(OC(NC(=NC(OCCCC)=O)SC)=O)CCC.COC(NC(=NC(OC)=O)SC)=O>>[N:100]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:104][CH:101]=1

Participants

16

Reactant 15

HCID 996PhenolHCID 2879P-CresolHCID 72452-ChlorophenolHCID 73763-(Trifluoromethyl)phenolHCID 74694'-HydroxyacetophenoneHCID 78084-BromophenolHCID 79333-ChlorophenolHCID 90154-MethoxyphenolHCID 97324-FluorophenolHCID 97433-FluorophenolHCID 130194-CyanophenolHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 54189253HCID 54189253, compoundHCID 56625616HCID 56625616, compoundHCID 57213372HCID 57213372, compound

Product 1

HCID 5798Benzimidazole

Procedure

In a similar manner, using phenol, p-cresol, o-chlorophenol, m-chlorophenol, o,p-dichlorophenol, m,p-dichlorophenol, m-trifluoromethylphenol, p-bromophenol, p-fluorophenol, m-fluorophenol, p-acetylphenol, p-cyanophenol, m-hydroxyphenol, and p-methoxyphenol in place of p-chlorophenol, the corresponding 1,2-diamino-4-phenoxy (or substituted phenoxy) benzenes and 2-carbomethoxyamino-5(6)-phenoxy (or substituted phenoxy) benzimidazole compounds are prepared. Using the 1,2-diamino compounds prepared above in this Example, and substituting 1,3-bis-ethoxycarbonyl-S-methyl isothiourea, 1,3-bis-propoxycarbonyl-S-methyl isothiourea, or 1,3-bis-butoxycarbonyl-S-methyl isothiourea for the 1,3-bis-methoxycarbonyl-S-methyl isothiourea, the corresponding 2-carbalkoxyamino-5(6)-phenoxy (or p-substituted phenoxy) benzimidazole compounds are prepared, where R is ethyl, propyl or butyl.

Workup

  1. customthe corresponding 1,2-diamino-4-phenoxy (or substituted phenoxy) benzenes and 2-carbomethoxyamino-5(6)-phenoxy (or substituted phenoxy) benzimidazole compounds are prepared

Sources & evidence

ORD record
ord-17e71ba7e94f448c86aa9a6c2518fe73
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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