Dimethylformamide → HCID 20770875, compound

HRID 591402Notes

Reaction equation

HRID 591402 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.CN(C=O)C.Cl[CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21].C([O-])([O-])=O.[K+].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:10][CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 36240Methyl 4-chloroacetoacetateHCID 22504773HCID 22504773, compound

Product 1

HCID 20770875HCID 20770875, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-chloro-5-methoxybenzenethiol (2.1 g) and DMF (dry) (30 mL) were added methyl 4-chloroacetoacetate (1.407 mL) and K2CO3 (1.994 g) at 0° C., and the mixture was stirred at room temperature for 5 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.440 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-d93bef30ad054a74916d425166210f33
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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