4-Methylbenzenethiol → HCID 15258981, compound

HRID 2055667Notes

Reaction equation

HRID 2055667 reaction equation
[O-][CH2:2][CH3:3].[Na+].[N+:5]([C:8]([C:12]([Cl:16])=[C:13]([Cl:15])[Cl:14])=[C:9](Cl)Cl)([O-:7])=[O:6].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1>C(O)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][C:9]([S:24][C:21]2[CH:22]=[CH:23][C:2]([CH3:3])=[CH:19][CH:20]=2)=[C:8]([N+:5]([O-:7])=[O:6])[C:12]([Cl:16])=[C:13]([Cl:15])[Cl:14])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 379884NSC665076HCID 2723922Sodium ethoxide

Product 1

HCID 15258981HCID 15258981, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., 5.05 g (75 mmol) of sodium ethoxide in 10 ml of ethanol are added dropwise over a period of 10 min to a solution of 10.00 g (36.9 mmol) of 2-nitropentachloro-1,3-butadiene and 9.3 g (75 mmol) of 4-methylthiophenol in 50 ml of ethanol. After 2 h of stirring at 0° C., the precipitate is separated off, washed with water and cold methanol (2×20 ml) and dried under reduced pressure, yield 14.5 g (88%), Rf=0.68 (Et2O: petroleum ether=1:3), m.p. 117-118° C.

Workup

  1. customthe precipitate is separated off
  2. washwashed with water and cold methanol (2×20 ml)
  3. dry with materialdried under reduced pressure, yield 14.5 g (88%), Rf=0.68 (Et2O: petroleum ether=1:3), m.p. 117-118° C.

Sources & evidence

ORD record
ord-33a43f0f60c641c5b645edc8175abad0
Source dataset
uspto-grants-2008_02
Patent number
US07332512B2

Reaction notes

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