Chloromethyl Methyl Ether → HCID 19898303, compound

HRID 1196401Notes

Reaction equation

HRID 1196401 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[N:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[N:23]=3)[C:13]=2[C:14]([OH:16])=[O:15])[N:4]=1.[H-].[Na+].[H][H].Cl[CH2:37][O:38][CH3:39]>CN(C)C=O.C(OCC)(=O)C>[CH3:29][O:28][C:26]1[CH:25]=[C:24]([O:30][CH3:31])[N:23]=[C:22]([O:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:12]([O:11][C:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=3)[C:13]=2[C:14]([O:16][CH2:37][O:38][CH3:39])=[O:15])[N:27]=1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 443031BispyribacHCID 178418361HCID 178418361, compound

Product 1

HCID 19898303HCID 19898303, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 g (3.5 mmol) of 2,6-bis[(4.6-dimethoxypyrimidin-2-yl)oxy]benzoic acid was dissolved in N,N-dimethylformamide, and 0.1 g of 60% sodium hydride was added to the resultant solution with stirring. After the generation of hydrogen ceased, 0.4 g of chloromethylmethylether was added to the solution and the resultant mixture was reacted at 100° C. for 3 hours. After completing the reaction, ice water and ethyl acetate were added to the reaction mixture, and the ethyl acetate layer was separated and washed with water. The washed ethyl acetate layer was then dried to be concentrated, and an oily product obtained thereby was subjected to column purification to obtain 1.0 g of a white crystal having a melting point of from 95° to 96° C.

Workup

  1. additionwere added to the reaction mixture
  2. customthe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialThe washed ethyl acetate layer was then dried
  5. concentrationto be concentrated
  6. customan oily product obtained
  7. customthereby was subjected to column purification

Sources & evidence

ORD record
ord-a420645674a54f8b9afc5425400c2243
Source dataset
uspto-grants-1992_05
Patent number
US05114463

Reaction notes

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