Dimethylformamide → HCID 117601739, compound

HRID 1773705Notes

Reaction equation

HRID 1773705 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[C:9]([I:23])[CH:8]=2)=[C:5]([CH3:24])[O:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.I[CH2:37][CH3:38]>CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([N:16]([CH2:37][CH3:38])[C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])=[C:9]([I:23])[CH:8]=2)=[C:5]([CH3:24])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 117601678HCID 117601678, compound

Product 1

HCID 117601739HCID 117601739, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitrophenyl)-2,2,2-trifluoroacetamide (2.2 g, 4.83 mmol), cesium carbonate (3.94 g, 12.08 mmol) and N,N-Dimethylformamide (100 ml) was stirred at room temperature under argon. To the mixture was added iodoethane (3.77 g, 24.17 mmol) and reaction was heated to 45° C. overnight. Crude mixture was diluted in EtOAc and water and extracted 3 times with EtOAc. Organics were washed with water, aq LiCl, then brine, dried over sodium sulfate and evaporated to dryness under reduced pressure to afford crude N-(4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitrophenyl)-N-ethyl-2,2,2-trifluoroacetamide as a dark oil.

Workup

  1. additionTo the mixture was added
  2. temperaturewas heated to 45° C. overnight
  3. extractionwater and extracted 3 times with EtOAc
  4. washOrganics were washed with water, aq LiCl
  5. dry with materialbrine, dried over sodium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-61936dd5cf6647a1bbe5463521af7a5a
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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