(2,4-Dichlorophenoxy)Acetic Acid → 2-(2,4-dichloro-phenoxy)-N-[3-(2-hydroxy-ethanesulfonyl)-phenyl]-acetamide

HRID 1945400Notes

Reaction equation

HRID 1945400 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:14][C:15]1[CH:16]=[C:17]([S:21]([CH2:24][CH2:25][OH:26])(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH2:24][CH2:25][OH:26])(=[O:23])=[O:22])[CH:16]=1)=[O:8]

Participants

7

Reactant 5

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 78905Ethanol, 2-[(3-aminophenyl)sulfonyl]-HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 248113262-(2,4-dichloro-phenoxy)-N-[3-(2-hydroxy-ethanesulfonyl)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,4-dichlorophenoxyacetic acid (110.6 mg, 0.5 mmol), 2-(3-amino-benzenesulfonyl)-ethanol (151.0 mg, 0.75 mmol), N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (143.8 mg, 0.75 mmol) and 1-hydroxybenzotriazole (HOBt) (102.1 mg, 0.75 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.13 ml, 0.75 mmol). The mixture was stirred overnight and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by preparative (CH2CH2:MeOH=30:1) to give 2-(2,4-dichloro-phenoxy)-N-[3-(2-hydroxy-ethanesulfonyl)-phenyl]-acetamide as a yell foam (21.5 mg, 10.6% yield).

Workup

  1. distillationredistilled (DIPEA) (0.13 ml, 0.75 mmol)
  2. custompartitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative (CH2CH2:MeOH=30:1)

Sources & evidence

ORD record
ord-ca0825bba0fc4c97b35c664d523bf86f
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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