Trifluoroacetic acid → HCID 86760281, compound

HRID 1245450Notes

Reaction equation

HRID 1245450 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:25]=[CH:24][C:14]([CH2:15][NH:16]C(=O)OC(C)(C)C)=[CH:13][CH:12]=1.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[NH2:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21912500HCID 21912500, compound

Product 1

HCID 86760281HCID 86760281, compound

Procedure

tert-Butyl 4-{[(2-aminoanilino)carbothioyl]amino}benzylcarbamate (4.3 g; 11.54 mmol) was refluxed in analogy to 21c with 5 g of HgO (yellow) and 0.05 g of sulfur in 150 ml of ethanol. Filtration of the reaction mixture through Celite and concentration afforded 2.1 g of a dark solid (ESI-MS [M+H+]=339.15). The tert-butyl 4-(1H-benzimidazol-2-ylamino)benzylcarbamate obtained in this way was treated without further purification with 15 ml of TFA at RT for 2 h, and concentration afforded 4.7 g of a dark oil which was reacted further without further purification (ESI-MS [M+H+]=239.05).

Workup

  1. concentrationconcentration

Sources & evidence

ORD record
ord-6f17b92ebb6748cc9db85a9583a64d41
Source dataset
uspto-grants-2006_10
Patent number
US07125883B1

Reaction notes

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