Dimethylformamide → ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate

HRID 1735897Notes

Reaction equation

HRID 1735897 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1=[S:23].[Cl-].CC=[N+]=CC.[CH3:30][N:31]([CH:33]=O)[CH3:32]>>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:14][N:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1=[S:23]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 19699405ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionateHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

HCID 19699336ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]propionate (0.5. g, 1.5 mmol), prepared as in Example 34, and N,N-dimethylmethyleneammonium chloride (0.17 g, 1.8 mmol) in 7 mL of DMF was heated at 80° C. under nitrogen for 16 hours. The mixture then was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic layer was separated, washed with brine, dried (NaSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane to give ethyl 3-[3-(1,2,3,4-tetrahydronaphthalen-2-yl)-4-dimethylaminomethyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl]-propionate (277 mg, 0.7 mmol), m.p. 128°-130° C.

Workup

  1. customThe mixture then was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-d64c48f57e654a74a94c9eb87ec68c82
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

Loading…