1,2-Dichloroethane → HCID 17231769, compound

HRID 1945419Notes

Reaction equation

HRID 1945419 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])=[O:7].[CH3:23][NH:24][CH3:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([N:24]([CH3:25])[CH3:23])=[O:13])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 668139HCID 668139, compound

Product 1

HCID 17231769HCID 17231769, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

To solution of 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid (100 mg, 0.29 mmol), dimethylamine (0.031 ml, 0.59 mmol) in DMF 3.0 mL was added EDC (83.4 mg, 0.44 mmol), HOBt (58.9 mg, 0.44 mmol) and DIPEA (0.076 ml, 0.44 mmol). Reaction mixture was stirred at room temperature, and separated by EtoAC and brine. The organic phase was dried (MgSO4 anh) and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1) to give 3-[2-(2,4-dichloro-phenoxy)acetylamino]-N,N-dimethyl-benzamide as a white solid (59.3 mg, 56% yield).

Workup

  1. customReaction mixture
  2. customseparated by EtoAC and brine
  3. dry with materialThe organic phase was dried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1)

Sources & evidence

ORD record
ord-8f9a18b8c544459bad4e3f9044900bb4
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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