Water → Mandipropamid

HRID 1092910Notes

Reaction equation

HRID 1092910 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:23][CH2:24][C:25]#[CH:26])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Cl)[C:34]#[CH:35].O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:23][CH2:24][C:25]#[CH:26])[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:35][C:34]#[CH:33])=[C:16]([O:21][CH3:22])[CH:15]=2)=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 235836252-(4-Chlorophenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-prop-2-ynoxyacetamide2×

Product 1

HCID 11292824MandipropamidYield 76.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 1 mol 2-(4-Chloro-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide in 500 ml toluene, 207 g potassium carbonate (1.5 mole) and 10 g tetrabutylammonium bromide are added. The mixture is heated to 90° C. and 1.4 mole propargyl chloride as a 35% solution in toluene is added over 30 minutes. After 3 hours the conversion of 2-(4-Chloro-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide is complete. To dissolve the salts 500 ml water are added and separated from the toluene product phase. The toluene is completely evaporated at 80° C./20 mbar and replaced by methanol. The product 2-(4-Chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide is crystallized from solution by cooling down to 0° C., filtered and washed with 200 ml methanol of 0° C. The product is dried at 50° C. under vacuum. 315 g of 2-(4-Chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide are obtained with a LC purity of 98%. Melting point=94-96° C.

Workup

  1. additionare added
  2. customseparated from the toluene product phase
  3. customThe toluene is completely evaporated at 80° C./20 mbar
  4. customThe product 2-(4-Chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide is crystallized from solution
  5. temperatureby cooling down to 0° C.
  6. filtrationfiltered
  7. washwashed with 200 ml methanol of 0° C
  8. customThe product is dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-b3717000301e43e8beed19c49b9f3f48
Source dataset
uspto-grants-2012_03
Patent number
US08129560B2

Reaction notes

Loading…