Diisopropylethylamine → HCID 66987535, compound

HRID 555278Notes

Reaction equation

HRID 555278 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][NH2:7])(=[O:4])=[O:3].CCN(C(C)C)C(C)C.[CH3:17][O:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][C:23](F)=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1>CN(C=O)C.O>[CH3:17][O:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][C:23]([NH:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 43405612-(Methylsulfonyl)ethanamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 66987535HCID 66987535, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methanesulfonylethylamine (1.3 g, 10.56 mmol) and DIPEA (3.5 mL, 31.69 mmol) in DMF (15 mL) was added 4-fluoro-3-nitro-benzoic acid methyl ester (1.2 g, 15.84 mmol) in portions. The reaction mixture was allowed to stir for 15 h at room temperature. It was then diluted with water and extracted with EtOAc. The organic layers were washed with water, brine and concentrated to give 4-(2-methanesulfonyl-ethylamino)-3-nitro-benzoic acid methyl ester (83%). 1H NMR (300 MHz, CDCl3) δ 8.9 (d, 1H), 8.6 (t, 1H), 8.2 (d, 1H), 6.9 (d, 1H), 4.0 (q, 2H), 3.9 (s, 3H), 3.4 (t, 2H), 3.0 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with water, brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a780a6e5b77b49c3b6324f4be2bd2203
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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