N-methyl-2-pyrrolidone → HCID 67158186, compound

HRID 30197Notes

Reaction equation

HRID 30197 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[C:20]([C:22]2[N:23]=[C:24]([CH3:34])[S:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[O:21])[O:11][CH:12]=1.[CH3:35][N:36]1C(=O)CCC1>C(OCC)(=O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]2[S:25][C:24]([CH3:34])=[N:23][C:22]=2[C:20]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]2[CH2:13][C:10]2[O:11][CH:12]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[C:35]#[N:36])[N:9]=2)=[O:21])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 67157913HCID 67157913, compound

Product 1

HCID 67158186HCID 67158186, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of the bromide (0.240 g) of example 176, Cu(I)CN (0.060 g) and N-Methyl pyrrolidinone (5 ml) was heated at 180° C. for 16 h. The cooled reaction mixture was diluted with ethyl acetate and passed through kiesselguhr, washing with ethyl acetate. The filtrate was washed with water, dried (sodium sulfate) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 20-50% ethyl acetate-pentane) to give the title compound as a pale yellow gum (0.101 g

Workup

  1. customThe cooled reaction mixture
  2. washwashing with ethyl acetate
  3. washThe filtrate was washed with water
  4. dry with materialdried (sodium sulfate) and solvent
  5. customremoved at reduced pressure
  6. customchromatographed (silica gel, 20-50% ethyl acetate-pentane)

Sources & evidence

ORD record
ord-e63acf1c8d3043a281c267d527930b00
Source dataset
uspto-grants-2008_09
Patent number
US07423052B2

Reaction notes

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