Diisopropylethylamine → 2-Nitro-5-(3-trifluoromethylbenzylthio)-p-xylene

HRID 2181583Notes

Reaction equation

HRID 2181583 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][SH:7].C(N(C(C)C)CC)(C)C.Cl[C:23]1[CH:24]=[C:25]([CH3:33])[C:26]([N+:30]([O-:32])=[O:31])=[CH:27][C:28]=1[CH3:29]>CN1CCCC1=O>[N+:30]([C:26]1[CH:27]=[C:28]([CH3:29])[C:23]([S:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[CH:24][C:25]=1[CH3:33])([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1412363-(Trifluoromethyl)benzyl mercaptanHCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 224812392-Nitro-5-(3-trifluoromethylbenzylthio)-p-xylene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-trifluoromethylbenzyl mercaptan (3.42 g), diisopropylethylamine (2.3 g) and 3-chloro-6-nitro-p-xylene (3.0 g) in dry N-methylpyrrolidinone (20 ml) was heated at 130° C. for 6 hours. On cooling, the mixture was poured into ice-water and the resulting mixture was filtered to give a solid which was washed with ice-water and then air dried. The solid was purified by silica gel chromatography eluting with light petroleum (60-80° C.)/ethyl acetate (9:1) to give the title product as a solid, m.p. 85-7° C.

Workup

  1. temperatureOn cooling
  2. filtrationthe resulting mixture was filtered
  3. customto give a solid which
  4. washwas washed with ice-water
  5. customair dried
  6. customThe solid was purified by silica gel chromatography
  7. washeluting with light petroleum (60-80° C.)/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-3c5c4555a8be471c84011d0e7e10a7b2
Source dataset
uspto-grants-2005_05
Patent number
US06893650B1

Reaction notes

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