Chlorosuccinimide → HCID 18931332, compound

HRID 1598986Notes

Reaction equation

HRID 1598986 reaction equation
[CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14].[Cl:17]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[C:9]([Cl:17])[C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18931181HCID 18931181, compound

Product 1

HCID 18931332HCID 18931332, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-methoxy-N-methyl-2,4-dimethoxybenzamide (7.2 g, 32 mmol), prepared as in Example 4, N-chlorosuccinimide (4.8 mL, 36 mmol) and acetonitrile (100 mL) was heated 16 hours at 50° C. The mixture was concentrated and the residue was partitioned between ethyl acetate (300 mL) and saturated sodium bicarbonate (150 mL). The mixture was filtered and the organic layer was separated, washed with water (4×) and brine (1×), dried (K2CO3), filtered through a short column of silica-gel and concentrated to give N-methoxy-N-methyl-5-chloro-2,4-dimethoxybenzamide (5.3 g, 20 mmol), m.p. 97°-99° C.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate (300 mL) and saturated sodium bicarbonate (150 mL)
  3. filtrationThe mixture was filtered
  4. customthe organic layer was separated
  5. washwashed with water (4×) and brine (1×)
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered through a short column of silica-gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-201f8f32056b4fe79ef230b8043dbd87
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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