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4-Aminobenzoic Acid → Benzimidazole

HRID 33756
Notes
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Reaction equation

HRID 33756 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1.[N-:18]=[C:19]=[S:20].C(Cl)(Cl)=S.[C:25]([CH2:27][C:28]([NH2:30])=[O:29])#[N:26]>>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:15][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:16][CH:17]=1.[S:20]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:18]=[CH:19]1.[N:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:26][CH:25]=1.[C:19]([CH:27]([C:25]#[N:26])[C:28]([NH2:30])=[O:29])(=[S:20])[NH2:18]
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 6115AnilineHCID 7898CyanoacetamideHCID 10040ThiophosgeneHCID 178418790HCID 178418790, compound

Product 4

HCID 5798BenzimidazoleHCID 7222Benzothiazole
HCID 88733Benzenamine, 4-(2-benzoxazolyl)-
HCID 13573014Thiocarbamoyl cyanoacetamide

Procedure

The 2-(4-aminophenyl)benzoxazole, benzothiazole, or benzimidazole was prepared by condensation of the appropriate aniline derivative with p-amino benzoic acid using polyphosphoric acid. The product was converted to the corresponding isothiocyanate with thiophosgene and subsequently condensed with cyanoacetamide to form the thiocarbamoyl cyanoacetamide. Treatment with bromine afforded the cyano hydroxy thiazole, which was converted to carboxamidine by treatment with the appropriate amide, as shown above.

Sources & evidence

ORD record
ord-ffad715435b24c70909bdbc409e32c04
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429667B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes