Diethyl Ether → 5-Bromo-2-[3-(2,2,2-trichloro-ethanoyl)-ureido]-thiophene-3-carboxylic Acid Amide

HRID 2223357Notes

Reaction equation

HRID 2223357 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]([Cl:26])([Cl:25])[C:11]([NH:13][C:14](=[O:24])[NH:15][C:16]1[S:17][CH:18]=[CH:19][C:20]=1[C:21]([NH2:23])=[O:22])=[O:12].C(OCC)C>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:1][C:18]1[S:17][C:16]([NH:15][C:14]([NH:13][C:11](=[O:12])[C:10]([Cl:9])([Cl:25])[Cl:26])=[O:24])=[C:20]([C:21]([NH2:23])=[O:22])[CH:19]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 597154532-[3-(2,2,2-Trichloro-ethanoyl)-ureido]-thiophene-3-carboxylic Acid Amide

Product 1

HCID 592436175-Bromo-2-[3-(2,2,2-trichloro-ethanoyl)-ureido]-thiophene-3-carboxylic Acid AmideYield 97.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.56 g, 8.8 mmol) was added to a solution of 2-[3-(2,2,2-trichloro-ethanoyl)-ureido]-thiophene-3-carboxylic acid amide (2.9 g, 8.8 mmol) in acetic acid (30 mL) and chloroform (10 mL) at room temperature. The resulting solution was stirred under nitrogen with an aliquot was taken for LC-MS every 10 min. After 30 min., the LC-MS showed no remaining starting material. Diethyl ether (80 mL) was added to the solution and the resulting precipitate was filtered and dried under vacuum to give the above titled compound as a light brown solid (3.5 g, 8.55 mmol, 97% yield).

Workup

  1. waitAfter 30 min.
  2. filtrationthe resulting precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-92f5e22493de463e83b968452c3e1fe0
Source dataset
uspto-grants-2008_05
Patent number
US07375131B2

Reaction notes

Loading…