Ethylamine → HCID 59591390, compound

HRID 1666574Notes

Reaction equation

HRID 1666574 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl[S:13]([OH:16])(=O)=[O:14].C(OCC)(=O)C.[CH2:23]([NH2:25])[CH3:24]>C1COCC1>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[C:9]([S:13]([NH:25][CH2:23][CH3:24])(=[O:16])=[O:14])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8857Ethyl AcetateHCID 24638Chlorosulfonic acidHCID 3029313-Chloro-2-fluorobenzoic acid

Product 1

HCID 59591390HCID 59591390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-chloro-2-fluorobenzoic acid (200 mg, 1.146 mmol) in chlorosulfonic acid (1.535 ml, 22.92 mmol) was stirred at room temperature for 30 seconds, then microwaved at 200 degrees for 10 rains. The reaction mixture was cooled to room temperature and dumped on ice (10 g) slowly. Ethyl acetate (25 ml) was added and extracted twice with ethyl acetate (10 mL X2). The combined organic phase was dried over MgSO4. Ethylamine (1833 μl, 3.67 mmol) in THF (2.0 M) was added, stirred at room temperature for 10 mins and washed with 1 N HCl (10 ml). The organic phase was dried over MgSO4 and concentrated to give the title compound, which was carried the next step without further purification.

Workup

  1. custommicrowaved at 200 degrees for 10 rains
  2. extractionextracted twice with ethyl acetate (10 mL X2)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. washwashed with 1 N HCl (10 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6563ce5547464d80912a31484c2baaef
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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