2,6-Dichlorophenoxyacetic acid → HCID 18603263, compound

HRID 745266Notes

Reaction equation

HRID 745266 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.S(Cl)(Cl)=O.[CH3:18][NH:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH:26][CH3:27]>ClCCl>[ClH:1].[Cl:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][C:6]([N:19]([CH3:18])[C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH:26][CH3:27])=[O:8]

Participants

5

Reactant 3

HCID 113322,6-Dichlorophenoxyacetic acidHCID 24386Thionyl ChlorideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 18603263HCID 18603263, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,6-dichlorophenoxyacetic acid (0.50 g, 2.3 mmol) was treated with thionyl chloride (6 ml) at room temperature for 60 hours. The solution was concentrated in vacuo to give an oil which was dissolved in dichloromethane (2.5 ml) and added dropwise over three minutes to a stirred solution of trans-(±)-N,N'-dimethylcyclohexane-1,2-diamine (0.35 g, 3.1 mmol) in dichloromethane (2.5 ml). After 1.5 hours at room temperature the mixture was filtered and the filtrate treated with diethyl ether until precipitation occurred. The resulting white solid was recrystallized (dichloromethane-diethyl ether) to give trans-(±)-2-(2,6-dichlorophenoxy)-N-methyl-N-[2-(methylamino)cyclohexyl]acetamide monohydrochloride (171 mg, 19%); VmaxC=0 (liquid file) 1655 cm-1.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give an oil which
  3. filtrationAfter 1.5 hours at room temperature the mixture was filtered
  4. additionthe filtrate treated with diethyl ether until precipitation
  5. customThe resulting white solid was recrystallized (dichloromethane-diethyl ether)

Sources & evidence

ORD record
ord-ac2c55efc5a946d8bf897995bdd6ecb9
Source dataset
uspto-grants-1986_07
Patent number
US04598087

Reaction notes

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