Methanol → HCID 18991968, compound

HRID 375509Notes

Reaction equation

HRID 375509 reaction equation
CO.[CH2:3]([O:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:9]=1[N+:20]([O-:22])=[O:21])[CH2:4][CH2:5][CH3:6].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1.C[O-].[Na+]>O>[C:24]1([CH3:23])[CH:29]=[CH:28][C:27]([S:30][C:13]2[C:8]([O:7][CH2:3][CH2:4][CH2:5][CH3:6])=[C:9]([N+:20]([O-:22])=[O:21])[CH:10]=[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 78114-MethylbenzenethiolHCID 66635Benzene, 1,4-dibutoxy-2-chloro-5-nitro-HCID 10942334Sodium Methoxide

Product 1

HCID 18991968HCID 18991968, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 110 parts of methanol was added 51 parts of 2,5-dibutoxy-4-chloronitrobenzene, and the mixture was warmed to 50° C. A methanol (50 parts) solution of 21.5 parts of p-thiocresol and 9.8 parts of sodium methylate was added dropwise thereto over a period of about one hour to carry out a reaction therebetween. After completion of the dropwise addition, the reaction was further continued under reflux for 5 hours. After completion of the reaction, 85 parts of water was added to the reaction mixture to precipitate a crystal. The crystal was recovered by filtration and recrystallized from methanol to obtain 58.5 parts of 4-tolylthio-2,5-dibutoxynitrobenzene (m.p.: 44° to 45° C.).

Workup

  1. customa reaction
  2. additionAfter completion of the dropwise addition
  3. temperatureunder reflux for 5 hours
  4. additionwas added to the reaction mixture
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-83345b52780e4db3905dcbb802cdcca9
Source dataset
uspto-grants-1996_01
Patent number
US05486446

Reaction notes

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