Methanol → HCID 86749218, compound

HRID 375507Notes

Reaction equation

HRID 375507 reaction equation
CO.[CH2:3]([O:7][C:8]1[CH:13]=[C:12]([Cl:14])[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].Cl[C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1.C[O-].[Na+]>O>[Cl:14][C:12]1[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:9]([N+:20]([O-:22])=[O:21])=[C:8]([O:7][CH2:3][CH2:4][CH2:5][CH3:6])[C:13]=1[S:30][C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 7815p-ChlorothiophenolHCID 66635Benzene, 1,4-dibutoxy-2-chloro-5-nitro-HCID 10942334Sodium Methoxide

Product 1

HCID 86749218HCID 86749218, 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. The mixture was heated to 50° C. A methanol (50 parts) solution of 25 parts of p-chlorobenzenethiol and 9.8 parts of sodium methylate was added dropwise thereto over a period of about one hour to carry out a reaction. 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 were added to the reaction mixture to precipitate a crystal. The resulting crystal was recovered by filtration and recrystallized from methanol to obtain 59 parts of 4-chlorophenylthio-2,5-dibutoxynitrobenzene having a m.p. of 74° to 75° C.

Workup

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

Sources & evidence

ORD record
ord-4efdc5f5789d4090b68d18a3a93cf143
Source dataset
uspto-grants-1996_01
Patent number
US05486446

Reaction notes

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