Ammonium Hydroxide → HCID 66749598, compound

HRID 537046Notes

Reaction equation

HRID 537046 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([OH:16])=O.C1C=CC2N(O)N=[N:23]C=2C=1.CCN=C=NCCCN(C)C.[NH4+].[OH-]>C(Cl)Cl.CN(C=O)C.O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:13])=[N:10][C:9]=1[C:14]([NH2:23])=[O:16]

Participants

9

Reactant 4

HCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66749736HCID 66749736, compound

Product 1

HCID 66749598HCID 66749598, compoundYield 90.1%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylic acid (20.0 g, 57.3 mmol) in DCM (400 mL) and DMF (200 mL) were added HOBt (8.0 g, 60.0 mmol) and EDCI (15.0 g, 80.0 mmol). The reaction mixture was allowed to stir at rt for 2 h and then NH4OH (20 mL) in 1,4-dioxane (400 mL) was added. The reaction mixture was allowed to stir at rt overnight and then was diluted with EtOAc and washed with brine. The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxamide (18.0 g, 85%).

Workup

  1. stirringto stir at rt overnight
  2. washwashed with brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2f3cf41d411544e398b7187887a4ca09
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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