Tetrachlorophthalic anhydride → HCID 86667327, compound

HRID 1506809Notes

Reaction equation

HRID 1506809 reaction equation
Cl.NC1NC2C=C(NC(C3C=CC=CC=3C(O)=O)=O)C=CC=2N=1.[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:30](C(OC(C)(C)C)=O)[C:29]=2[CH:55]=1.[Cl:56][C:57]1[C:65]([Cl:66])=[C:64]([Cl:67])[C:63]([Cl:68])=[C:62]2[C:58]=1[C:59](=[O:70])[O:60][C:61]2=[O:69]>>[ClH:56].[NH2:33][C:31]1[NH:30][C:29]2[CH:55]=[C:25]([NH:24][C:61]([C:62]3[C:63]([Cl:68])=[C:64]([Cl:67])[C:65]([Cl:66])=[C:57]([Cl:56])[C:58]=3[C:59]([OH:70])=[O:60])=[O:69])[CH:26]=[CH:27][C:28]=2[N:32]=1

Participants

4

Reactant 3

HCID 8326Tetrachlorophthalic anhydrideHCID 67531620HCID 67531620, compoundHCID 67531839HCID 67531839, compound

Product 1

HCID 86667327HCID 86667327, compoundYield 154.4%

Procedure

Following the same procedure to synthesize 2-(2-amino-1H-benzo[d]imidazol-6-ylcarbamoyl)benzoic acid hydrochloride, tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.100 g, 0.223 mmol) was reacted with 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (0.064 g, 0.223 mmol) to give the title compound (0.081 g, 77% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.32 (s, 2H), δ 7.12 (s, 1H) ppm; 13C NMR (75 MHz, CD3OD) δ 198.8, 165.5, 152.2, 134.7, 133.5, 130.6, 130.2, 129.6, 126.5, 118.5, 112.5, 106.7 ppm; HRMS (ESI) Calcd for C15H8Cl4N4O3 (M+) 431.9351. Found 431.9359.

Sources & evidence

ORD record
ord-aacc53838a53496fbe2521d3b901a21c
Source dataset
uspto-grants-2015_12
Patent number
US09221765B2

Reaction notes

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