Dimethylformamide → 8-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxamide

HRID 1593619Notes

Reaction equation

HRID 1593619 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14](O)=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:17]=1.C(Cl)(=O)C(Cl)=O.C[N:25](C=O)C>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14]([NH2:25])=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 692352028-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylic acid

Product 1

HCID 692322118-Fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylic acid (1.2 g, 4.8 mmol) in CH2Cl2 (20 mL) was added oxalyl chloride (0.55 mL, 6.24 mmol) and a drop of DMF. The reaction was stirred at room temperature for 30 min, then was concentrated in vacuo. The resulting residue was dissolved in acetone (30 mL) and cooled to −5° C. Conc. NH4OH (10 mL) was added quickly, resulting in a white precipitate. The suspension was stirred for 30 min, then diluted with water and filtered to afford 1.14 g (95%) of the title compound as a white solid: mp 201-202° C.; MS (−) 248 (M−H)−.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in acetone (30 mL)
  3. temperaturecooled to −5° C
  4. additionConc. NH4OH (10 mL) was added quickly
  5. customresulting in a white precipitate
  6. stirringThe suspension was stirred for 30 min
  7. filtrationfiltered

Sources & evidence

ORD record
ord-550c2a34f7984a67818852460d39bf96
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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