Isopropylamine → 2-(4-Amino-phenyl)-ethanesulfonic acid isopropylamide

HRID 1989038Notes

Reaction equation

HRID 1989038 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][S:12](Cl)(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[CH:16]([NH2:19])([CH3:18])[CH3:17]>C1COCC1>[CH:16]([NH:19][S:12]([CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1)(=[O:14])=[O:13])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 27611752-(4-nitrophenyl)ethanesulfonyl Chloride

Product 1

HCID 686791022-(4-Amino-phenyl)-ethanesulfonic acid isopropylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitro-phenyl)-ethanesulfonyl chloride (300 mg) was suspended in 5 mL of THF. To the stirring solution was added isopropylamine (600 μL) dropwise at r.t. After 5 hours the solvent was evaporated. The nitro product was purified by flash chromatography (CH2Cl2/CH3OH 10:1 v/v) and was converted to the title compound under normal hydrogenation conditions. The title compound was obtained as a yellow solid (182 mg, 54%). 1H NMR (300 MHz, CD3OD) δ (ppm): 6.96 (d, J=8.3 Hz, 2H), 6.69 (d, J=8.3 Hz, 2H), 3.53 (m, 1H), 3.19 (m, 2H), 2.91 (m, 2H), 1.20 (s, 3H), 1.18 (s, 3H).

Workup

  1. customAfter 5 hours the solvent was evaporated
  2. customThe nitro product was purified by flash chromatography (CH2Cl2/CH3OH 10:1 v/v)

Sources & evidence

ORD record
ord-73addc97134a4cb5bcc2e0d724b319c7
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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