Methanol → 3-[(Aminocarbonyl)amino]-5-(2-hydroxyphenyl)-2-thiophenecarboxamide

HRID 900423Notes

Reaction equation

HRID 900423 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]C)[S:7][C:6]=1[C:18]([NH2:20])=[O:19])=[O:3].B(Br)(Br)Br.CO>ClCCl>[NH2:1][C:2]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[S:7][C:6]=1[C:18]([NH2:20])=[O:19])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 9835679HCID 9835679, compound

Product 1

HCID 179309823-[(Aminocarbonyl)amino]-5-(2-hydroxyphenyl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[(Aminocarbonyl)amino]-5-(2-methoxyphenyl)-2-thiophenecarboxamide (0.1 g), boron tribromide (2 ml of a 1M solution in dichloromethane) and dichloromethane (10 mL) were stirred at room temperature for 16 h. Methanol (5 mL) was added and after 1 h, the solvent was evaporated. 2M Hydrochloric acid (10 mL) was added and, after stirring for 1 h, the phenol was filtered off and used directly in step (b).

Workup

  1. customthe solvent was evaporated
  2. addition2M Hydrochloric acid (10 mL) was added
  3. filtrationthe phenol was filtered off

Sources & evidence

ORD record
ord-6631b47902cc406987bd878b64626c75
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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