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

HRID 863086Notes

Reaction equation

HRID 863086 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-b4cba53e4cd54a9bb9eaa88ffaaf75c1
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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