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

HRID 549363Notes

Reaction equation

HRID 549363 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-42a3128734aa4c8881ef4dd4e9daf3b2
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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