Acetic Acid → HCID 59191313, compound

HRID 1023964Notes

Reaction equation

HRID 1023964 reaction equation
[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[F:18])=[C:5]([OH:21])[CH:4]=1)[CH3:2].[CH3:22]CN=C=NCCCN(C)C.[C:33]([OH:36])(=O)[CH3:34]>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:33](=[O:36])[CH3:34])(=[O:15])=[O:16])=[CH:10][C:9]=2[F:18])=[C:5]([O:21][CH3:22])[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59191278HCID 59191278, compound

Product 1

HCID 59191313HCID 59191313, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-ethyl-2-hydroxyphenoxy)-3-fluorobenzenesulfonamide (0.28 mmol; 90 mg) in anhydrous dichloromethane (1 mL), under argon were added EDAC (0.36 mmol; 69 mg), DMAP (0.31 mmol; 38 mg) and acetic acid (0.36 mmol; 0.02 mL). The reaction was stirred overnight at room temperature. Diluted with dichloromethane (3 mL), the mixture was washed with HCl (1N; 3 mL). The organic phase was dried over MgSO4, concentrated to yield the desired compound as a yellow foam (90 mg; 0.25 mmol; 89%), used as such in the following reaction.

Workup

  1. washthe mixture was washed with HCl (1N; 3 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5bf6b71060ad4c35b6c09c0581774054
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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