Methanol → 1-Methyl-4-[(1,3,4,4-tetrachloro-2-nitrobuta-1,3-dien-1-yl)sulfanyl]benzene

HRID 2055666Notes

Reaction equation

HRID 2055666 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[N+:9]([C:12]([C:16]([Cl:20])=[C:17]([Cl:19])[Cl:18])=[C:13](Cl)[Cl:14])([O-:11])=[O:10].CO>CCOCC>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:13]([Cl:14])=[C:12]([N+:9]([O-:11])=[O:10])[C:16]([Cl:20])=[C:17]([Cl:18])[Cl:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 78114-MethylbenzenethiolHCID 379884NSC665076

Product 1

HCID 713532881-Methyl-4-[(1,3,4,4-tetrachloro-2-nitrobuta-1,3-dien-1-yl)sulfanyl]benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At room temperature, 4.72 g (38 mmol) of 4-methylthiophenol are added to a solution of 10.00 g (36.9 mmol) of 2-nitropentachloro-1,3-butadiene in 20 ml of ether, and the mixture is stirred for 20 h. The ether is then removed under reduced pressure, and the crystal slurry which is formed after addition of 20 ml of methanol is filtered off, washed with cold MeOH (2×10 ml) and dried under reduced pressure, yield 9.9 g (75%), Rf=0.72 (Et2O: petroleum ether=1:3), m.p. 110-111° C.

Workup

  1. customThe ether is then removed under reduced pressure
  2. customthe crystal slurry which is formed
  3. filtrationis filtered off
  4. washwashed with cold MeOH (2×10 ml)
  5. dry with materialdried under reduced pressure, yield 9.9 g (75%), Rf=0.72 (Et2O: petroleum ether=1:3), m.p. 110-111° C.

Sources & evidence

ORD record
ord-eec9090e7b68484287415fe05c8b73b3
Source dataset
uspto-grants-2008_02
Patent number
US07332512B2

Reaction notes

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