2-Chloro-3-nitrotoluene → HCID 57436052, compound

HRID 1095396Notes

Reaction equation

HRID 1095396 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[CH3:12][S:13][CH2:14][CH2:15][NH2:16].C(N(CC)C(C)C)(C)C>CN1CCCC1=O.C(OCC)(=O)C>[CH3:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:16][CH2:15][CH2:14][S:13][CH3:12]

Participants

6

Reactant 3

HCID 775912-Chloro-3-nitrotoluene2×HCID 81531DiisopropylethylamineHCID 87697(2-(Methylthio)ethyl)amine

Product 1

HCID 57436052HCID 57436052, compoundYield 157.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 2-chloro-3-nitrotoluene (1.3 g, 7.3 mmol), 2-(methylthio)ethylamine (1.4 mL, 15 mmol) and N,N-diisopropylethylamine (5.0 mL, 29 mmol) in 1-methyl-2-pyrrolidinone (3.7 mL) was heated to 220° C. by microwave for 1 h. The mixture was diluted with ethyl acetate (0.10 L) and washed with water (50 mL×2), brine (50 mL), dried over sodium sulfate, filtered and concentrated to give a crude material. The another batch starting from 1.3 g of 2-chloro-3-nitrotoluene was combined to this crude material and the combined crude products were purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1) to afford 2.6 g (77%) of the title compound.

Workup

  1. washwashed with water (50 mL×2), brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude material
  6. customthe combined crude products were purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-6ed841d773a94560b61200e5cf266f5b
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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