Diisopropylamine → HCID 18672729, compound

HRID 1057989Notes

Reaction equation

HRID 1057989 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][CH2:13][C:14](Cl)=[O:15].COC1C=CC([N+]([O-])=O)=CC=1CCC(O)=O.S(Cl)(Cl)=O.[CH:37]([NH:40][CH:41]([CH3:43])[CH3:42])([CH3:39])[CH3:38]>ClCCl>[CH:37]([N:40]([CH:41]([CH3:43])[CH3:42])[C:14](=[O:15])[CH2:13][CH2:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 24386Thionyl ChlorideHCID 2404413-(2-methoxy-5-nitrophenyl)propanoic acidHCID 57054408HCID 57054408, compound

Product 1

HCID 18672729HCID 18672729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(2-methoxy-5-nitrophenyl)propionyl chloride(0.46 g, 1.9 mmol), prepared from 3-(2-methoxy-5-nitrophenyl)propionic acid (Asano et al., J. Pharm. Soc. Japan, 1950, 70, 480) and thionyl chloride, in dichloromethane (5 mL) was added in one portion to a solution of diisopropylamine (0.67 g, 6.6 mmol) in dichloromethane (20 mL), stirred for 16 h, washed with water (2×20 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound: MS(ES) m/3 309.1 [M+H]+.

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3eec206753d3459085622cddf1b41cec
Source dataset
uspto-grants-2003_02
Patent number
US06515027B1

Reaction notes

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