Diethyl Ether → HCID 67958972, compound

HRID 707650Notes

Reaction equation

HRID 707650 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[N:9][OH:10])=[CH:4][N:3]=1.ClN[C:13](=O)[CH2:14][CH2:15][C:16](N)=O.C(OCC)C.[CH3:25][Si:26](C#C)([CH3:28])[CH3:27]>CN(C=O)C.C(N(CC)CC)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:14]([C:15]#[C:16][Si:26]([CH3:28])([CH3:27])[CH3:25])[O:10][N:9]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 15238416N-chlorosuccinamideHCID 86706842HCID 86706842, compound

Product 1

HCID 67958972HCID 67958972, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 2-methyl-pyrimidine-5-carbaldehyde oxime (145 gm) in DMF (435 ml) was added N-chlorosuccinamide (169.6 gm) in portions at 30° C. for 0.5 h. As the TLC indicated completion of the reaction, diethyl ether (1450 ml) was added. The reaction mixture was cooled to −5° to 0° C. To a cooled reaction mixture, was added triethylamine (589 ml) followed by trimethylsilylacetylene (450 ml). The mixture was stirred at −5° C. for additional 1 h. The solid separated was filtered at suction. Filtrate was washed with water (300 ml×4) followed by brine solution (500 ml) and organic layer was concentrated under vacuum to provide a solid in 158 gm quantity which was used as it is for further reaction.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to −5° to 0° C
  3. customTo a cooled reaction mixture
  4. customThe solid separated
  5. filtrationwas filtered at suction
  6. washFiltrate was washed with water (300 ml×4)
  7. concentrationwas concentrated under vacuum
  8. customto provide a solid in 158 gm quantity which
  9. customis for further reaction

Sources & evidence

ORD record
ord-121d94e367c84576a6aa14f8b21536fe
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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