3-Bromo-1,1,1-trifluoro-2-propanone → HCID 59251584, compound

HRID 1466407Notes

Reaction equation

HRID 1466407 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=[NH:8])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27]>>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:9]([C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=3[Cl:17])[CH2:24][C:25]([C:26]([F:29])([F:28])[F:27])([OH:30])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178512050HCID 178512050, compound

Product 1

HCID 59251584HCID 59251584, compoundYield 99%

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-bromo-N-(2,5-dichloro-phenyl)-thiophene-2-carboxamidine (634 mg, 1.8 mmol) and sodium bicarbonate (227 mg, 2.7 mmol) in 8 mL 2-proponal was added 3-bromo-1,1,1-trifluoroacetone (520 mg, 2.7 mmol). The reaction mixture was heated at 50° C. for 1.5 hrs, then at 80° C. for 4 hrs. After cooling to room temperature, the residue was filtered out and washed with dichloromethane. The filtrate and washings were combined together and concentrated under vacuum to give a light pink solid that was used directly for the next step (820 mg, 99% yield). 1H-NMR (400 MHz, DMSO-d6): δ 3.09 (d, 1H), 3.95 (dd, 1H), 6.31 (d, 1H), 6.91 (d, 1H), 7.15 (m, 1H), 7.33 (dd, 1H), 7.44 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe residue was filtered out
  3. washwashed with dichloromethane
  4. concentrationconcentrated under vacuum
  5. customto give a light pink solid that

Sources & evidence

ORD record
ord-6344fe9919e04e32bd0d79e9ce1a792e
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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