Triethylamine → HCID 59623734, compound

HRID 1093950Notes

Reaction equation

HRID 1093950 reaction equation
[ClH:1].[F:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](C(F)(F)F)=[CH:16][C:15]=1[CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:1])[CH:17]=[CH:16][C:15]=1[CH2:24][S:25]([NH:5][CH2:4][CH2:3][F:2])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 59623758HCID 59623758, compound

Product 1

HCID 59623734HCID 59623734, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-fluoroethylamine hydrochloride (0.287 g) in dichloro-methane (4 ml) was added triethylamine (0.4 ml) followed by (2,4-dichloro-phenyl)-methanesulfonyl chloride (Example 1.2) (0.25 g). The reaction mixture was stirred at ambient temperature for 3 hours then left to stand at ambient temperature for 16 hours. Dichloromethane (20 ml) was added to the reaction mixture and the mixture was washed with water (20 ml). The phases were separated and the organic layer was dried over magnesium sulfate and concentrated to give C-(2,4-dichloro-phenyl)-N-(2-fluoro-ethyl)-methanesulfonamide (15 mg) (60% pure). 1H-NMR (400 MHz, CDCl3): 7.47-7.51 (m, 2H), 7.29-7.32 (dd, 1H), 4.77 (bs, 1H), 4.49 (s, 2H), 4.51-4.53 (m, 1H), 4.39-4.42 (m, 1H), 3.33-3.36 (m, 1H), 3.27-3.29 (m, 1H) ppm.

Workup

  1. waitthen left
  2. waitto stand at ambient temperature for 16 hours
  3. washthe mixture was washed with water (20 ml)
  4. customThe phases were separated
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-420c19f4aab648fb91843194c5077b56
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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