1,2-Dichloroethane → HCID 24811987, compound

HRID 1945426Notes

Reaction equation

HRID 1945426 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]([OH:14])=O)=[O:7].[CH2:23]([CH2:25][NH2:26])[OH:24].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]([NH:26][CH2:25][CH2:23][OH:24])=[O:14])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 668139HCID 668139, compound

Product 1

HCID 24811987HCID 24811987, compoundYield 80.1%

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 (150 mg, 0.44 mmol) and ethanolamine (0.04 ml, 0.66 mmol) in DMF 3.0 mL was added EDC (126.5 mg, 0.66 mmol), HOBt (89.2 mg, 0.66 mmol) and DIPEA (0.11 ml, 0.66 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=15:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(2-hydroxy-ethyl)-benzamide as a white solid (135 mg, 80% 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=15:1)

Sources & evidence

ORD record
ord-aa0a1d95c538438f856b262c3b99b15d
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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