4-Aminobenzoic Acid → Benzimidazole

HRID 1993815

反応式

HRID 1993815 の反応式
[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]

参加物

9

反応物 5

HCID 9784-Aminobenzoic AcidHCID 6115AnilineHCID 7898CyanoacetamideHCID 10040ThiophosgeneHCID 178418790HCID 178418790、化合物

生成物 4

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

実験手順

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.

出典と根拠

ORDレコード
ord-acf9ff7ba07e412e9887c036d410a8b1
出典データセット
uspto-grants-2010_01
特許番号
US07652047B2

関連ノート

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