Methanol → Methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate

HRID 2421845Notes

Reaction equation

HRID 2421845 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([CH3:19])([S:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH3:5].C(N(CC)CC)C.[CH3:27][OH:28]>>[Cl:1][CH2:2][CH2:3][C:4]([CH3:19])([S:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:28][CH3:27])=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])[CH3:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 86628743HCID 86628743, compound

Product 1

HCID 67242953Methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate

Procedure

To a solution of 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoyl chloride (3.48 g, 10.8 mmol) in MeOH (200 mL) was added triethylamine (15.05 mL, 108 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure. The resulting paste was diluted with EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (75 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting solid was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe resulting paste was diluted with EtOAc (200 mL)
  3. washwashed with saturated aqueous NaHCO3 (75 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was used without further purification

Sources & evidence

ORD record
ord-50eb4fa0580f489bac3c4157ca4fd66c
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

Loading…