Triethylamine → HCID 24670060, compound

HRID 925083Notes

Reaction equation

HRID 925083 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[CH3:15][NH:16][O:17][CH3:18].[CH2:19]([N:21](CC)[CH2:22]C)C.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[CH3:19][N:21]([CH3:22])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:16]([O:17][CH3:18])[CH3:15])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 679874-Fluoro-3-nitrobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 24670060HCID 24670060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzoic acid (5 g, 27.0 mmol) in dimethylformamide (100 mL) was added N,O-dimethylhydroxylamine hydrochloride (5.93 g, 60.8 mmol) and triethylamine (17.0 mL, 122 mmol). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (11.65 g, 60.8 mmol) and hydroxybenzotriazole (9.31 g, 60.8 mmol) were added and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated and partitioned between ethyl acetate (150 mL) and brine (150 mL). The organics were concentrated on rotary evaporator and the crude was purified by flash chromatography eluting with 40% ethyl acetate in hexanes to provide the title product. MS (DCI/NH3) m/z 254 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate (150 mL) and brine (150 mL)
  3. concentrationThe organics were concentrated on rotary evaporator
  4. customthe crude was purified by flash chromatography
  5. washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-da6527b4d9be4510ac3cc70b65b02455
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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