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1-(1,3-Dioxolan-2-yl)methanamine → N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide

HRID 1995044
Notes
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Reaction equation

HRID 1995044 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].[N+:8]([C:11]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:12]=1[O:13][CH:14]([CH2:18][CH3:19])[C:15](Cl)=[O:16])([O-:10])=[O:9]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:15](=[O:16])[CH:14]([O:13][C:12]1[CH:20]=[C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])[CH:22]=[CH:23][C:11]=1[N+:8]([O-:10])=[O:9])[CH2:18][CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 108553941-(1,3-Dioxolan-2-yl)methanamineHCID 204411292-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyryl chloride

Product 1

HCID 20441174N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

N-(1,3-Dioxolan-2-ylmethyl)amine (0.015 mole) triethylamine (5 ml) and methylene chloride (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The reaction mixture is cooled to about -15° C. and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butanoyl chloride (0.01 mole) in methylene chloride (50 ml) is added dropwise with stirring. After the addition is completed the reaction mixture is allowed to warm to room temperature with continued stirring. After this time the mixture is transferred to a separatory funnel and is washed with water and dilute aqueous sodium bicarbonate. The washed solution is then dried, filtered and stripped of solvent leaving a residue. The residue is then recrystallized from a toluene/hexane mixture to yield the desired product N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyramide.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. temperatureto warm to room temperature with continued stirring
  5. customAfter this time the mixture is transferred to a separatory funnel
  6. washis washed with water and dilute aqueous sodium bicarbonate
  7. customThe washed solution is then dried
  8. filtrationfiltered
  9. customleaving a residue
  10. customThe residue is then recrystallized from a toluene/hexane mixture

Sources & evidence

ORD record
ord-6d30d0b1563044c492d355d7f59049a9
Source dataset
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04402729

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes