Acetic Acid → HCID 86617314, compound

HRID 2364059Notes

Reaction equation

HRID 2364059 reaction equation
[CH3:1][C:2]1[C:3]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.C(O)(=O)C.[Br:22]N1C(=O)CCC1=O.O>[Cl-].[Na+].O>[Br:22][C:6]1[S:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[C:3]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 67184N-bromobutanimideHCID 86617313HCID 86617313, compound

Product 1

HCID 86617314HCID 86617314, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of methyl 4-methyl-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (11.7 g, 43.8 mmol) and acetic acid (150 mL) was added 1-bromopyrrolidine-2,5-dione (15.6 g, 88.0 mmol) at room temperature. Then, this mixture was stirred at 80° C. for 6 h. After cooling to room temperature, the mixture was poured into water (600 mL) and brine (300 mL). The precipitate was collected by filtration, washed with water, dried under vacuum to afford the title compound (9.40 g, 62%) as a white solid:

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5a0fd021e57841bfb690efae3ee04ed3
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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