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

HRID 900421Notes

Reaction equation

HRID 900421 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13]C)[CH:8]=2)[S:4][C:3]=1[C:15]([NH2:17])=[O:16].C[Si]([N:22]=[C:23]=[O:24])(C)C.CN(C)C=O>ClCCl>[NH2:22][C:23]([NH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[S:4][C:3]=1[C:15]([NH2:17])=[O:16])=[O:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 99648693-Amino-5-(3-methoxyphenyl)-2-thiophenecarboxamide

Product 1

HCID 99654243-[(Aminocarbonyl)amino]-5-(3-hydroxyphenyl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-5-(3-methoxyphenyl)-2-thiophenecarboxamide (0.5 g), trimethylsilylisocyanate (2 mL), dimethylformamide (2 mL) and dichloromethane were heated at reflux for 3 days. After cooling the solid was filtered off, suspended in dichloromethane (100 mL) and treated with boron tribromide (5 mL of a 1M solution in dichloromethane). After 3 days. methanol (50 mL) was added. After 1 h, the solvent was evaporated and the residue was triturated with 2M hydrochloric acid. The title urea was filtered off (0.35 g).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureAfter cooling the solid
  3. filtrationwas filtered off
  4. additiontreated with boron tribromide (5 mL of a 1M solution in dichloromethane)
  5. additionmethanol (50 mL) was added
  6. waitAfter 1 h
  7. customthe solvent was evaporated
  8. customthe residue was triturated with 2M hydrochloric acid
  9. filtrationThe title urea was filtered off (0.35 g)

Sources & evidence

ORD record
ord-cd440d8d0d8f4e91977ddd3af6825c5c
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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