Sulfuric Acid → HCID 15662574, compound

HRID 1073438Notes

Reaction equation

HRID 1073438 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12](OC)=[O:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].[CH3:18][NH2:19].C[O-].[Na+].S(=O)(=O)(O)O>CN(C=O)C>[CH3:1][CH:2]([O:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([NH:19][CH3:18])=[O:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 15662571HCID 15662571, compound

Product 1

HCID 15662574HCID 15662574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(1-methylpropoxy)phenoxyacetate (7.94 g, 33.3 mmol) in 65 ml of dry DMF at 0° and with stirring is added methylamine gas to saturation (ca. 25 min.). A trace of sodium methoxide (ca. 10 mg) is added and the mixture is allowed to warm to RT. After 20 hours at RT, the reaction mixture is poured into ice water and 10 ml of 3N sulfuric acid and extracted with ether. The combined organic phases are washed with water, with 10% sodium bicarbonate, with water and with brine, dried, filtered and the filtrate evaporated in vacuo to give 4-(1-methylpropoxy)phenoxy-N-methylacetamide.

Workup

  1. extractionextracted with ether
  2. washThe combined organic phases are washed with water, with 10% sodium bicarbonate, with water and with brine
  3. customdried
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-c1304fc78fe94c35afa476db138ef826
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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