Triethylamine → 3,3-dichloro-N-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl}-2-(4-trifluoromethyl-phenyl)-acrylamide

HRID 1869139Notes

Reaction equation

HRID 1869139 reaction equation
[Cl:1][C:2]([Cl:17])=[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[C:4]([OH:6])=O.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[Cl:40][C:41]1[CH:51]=[C:50]([O:52][CH2:53][CH:54]=[C:55]([Cl:57])[Cl:56])[CH:49]=[C:48]([Cl:58])[C:42]=1[O:43][CH2:44][CH2:45][CH2:46][NH2:47]>ClCCl.C(OCC)(=O)C>[Cl:17][C:2]([Cl:1])=[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[C:4]([NH:47][CH2:46][CH2:45][CH2:44][O:43][C:42]1[C:48]([Cl:58])=[CH:49][C:50]([O:52][CH2:53][CH:54]=[C:55]([Cl:57])[Cl:56])=[CH:51][C:41]=1[Cl:40])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 158697443-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propylamineHCID 866130803,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid

Product 1

HCID 112964533,3-dichloro-N-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propyl}-2-(4-trifluoromethyl-phenyl)-acrylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

74 mg of 3,3-dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid, 67 mg of bis(2-oxo-3-oxazolidinyl)-phosphinic acid chloride, 53 mg of triethylamine and 100 mg of 3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propylamine are stirred in 2 ml of dichloromethane for 48 hours at 40° C. The reaction mixture is diluted with 16 ml of ethyl acetate and washed twice with aqueous potassium carbonate solution. After concentration of the organic phase and purification over silica gel, the title compound is obtained.

Workup

  1. washwashed twice with aqueous potassium carbonate solution
  2. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-a20d22ad4fe74cfda6fd3bc395557689
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

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