Methane → N-(1,3-Dioxolan-2-ylmethyl)-2-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

HRID 1995036Notes

Reaction equation

HRID 1995036 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].C(N(CC)CC)C.[N+:15]([C:18]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=2[Cl:41])=[CH:26][C:19]=1[O:20][CH:21]([CH3:25])[C:22](Cl)=[O:23])([O-:17])=[O:16].C>C(Cl)Cl.C1(C)C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:26]=[C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=2[Cl:41])[CH:28]=[CH:29][C:18]=1[N+:15]([O-:17])=[O:16])[CH3:25]

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 108553941-(1,3-Dioxolan-2-yl)methanamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl Chloride

Product 1

HCID 13193074N-(1,3-Dioxolan-2-ylmethyl)-2-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-(1,3-Dioxolan-2-ylmethyl)amine (1.85 grams; 0.015 mole), triethylamine (5 ml) and methylene chloride (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture was cooled in a dry ice bath to a temperature of -20° C. to -10° C. and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (4.2 grams; 0.01 mole) in methylene chloride (50 ml) was added dropwise with stirring. After the addition was completed the reaction mixture was allowed to warm to room temperature with stirring over a period of about 1 hour. After this time the reaction mixture was transferred to a separatory funnel and washed with water (100 ml) with dilute aqueous sodium bicarbonate (200 ml; 5% concentration) and again with water (100 ml). The washed mixture was then dried by passing it through phase separation paper and was stripped of solvent in a rotary evaporator under reduced pressure leaving a white solid residue. This residue was dissolved in toluene, treated with activated charcoal and filtered. The filtrate was partially stripped of toluene and diluted with hexane to precipitate the desired product N-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as a white crystalline solid melting at 148° to 149.5° C.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. temperatureThe mixture was cooled in a dry ice bath to a temperature of -20° C. to -10° C.
  4. additionAfter the addition
  5. stirringwith stirring over a period of about 1 hour
  6. customAfter this time the reaction mixture was transferred to a separatory funnel
  7. washwashed with water (100 ml) with dilute aqueous sodium bicarbonate (200 ml; 5% concentration) and again with water (100 ml)
  8. customThe washed mixture was then dried
  9. customthrough phase separation paper
  10. customwas stripped of solvent in a rotary evaporator under reduced pressure
  11. customleaving a white solid residue
  12. filtrationfiltered
  13. additiondiluted with hexane
  14. customto precipitate the desired product N-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as a white crystalline solid melting at 148° to 149.5° C.

Sources & evidence

ORD record
ord-385b9738829a4f7ba6933dee8473ae62
Source dataset
uspto-grants-1983_09
Patent number
US04402729

Reaction notes

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