Triethylamine → HCID 53884514, compound

HRID 1885536Notes

Reaction equation

HRID 1885536 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[C:6](C)[CH:5]=1)#[N:2].Cl.N[CH2:16][CH2:17][SH:18].[CH2:19](N(CC)CC)C>CCO>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C:1]2[S:18][CH2:17][CH2:16][N:2]=2)=[CH:12][CH:11]=1)([O:10][CH3:19])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 53420858HCID 53420858, compound

Product 1

HCID 53884514HCID 53884514, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.75 g (10 mmol) of the above 4-(cyanomethyl) methyl benzoate (6) in 10 mL of EtOH was added 1.14 g (10 mmol) of cysteamine hydrochloride and 1.4 mL (10 mmol) of triethylamine. The reaction mixture was refluxed for 24 h. and evaporated to dryness. The residue was dissolved in CH2Cl2 (50 mL), washed with water and dried over Na2SO4. Removal of the solvent gave crude 7, which was crystallized from EtOH. Yield 2.1 g (89%); mp 67°-68° C.; NMR (CDCl3), δ8.0 (m, 2H, aromatic), 7.4 (m, 2H, aromatic), 4.2 (t, 2H, CH2), 3.9 (s, 3H CH3), 3.85 (s, 2H, CH2); IR (Nujol), 720 (ester), 1620 (C=N) cm-1 ; MS (EI) calculated for (C12H13NO2S), 235.00; found, 235 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h.
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. customgave crude 7, which
  8. customwas crystallized from EtOH

Sources & evidence

ORD record
ord-c4c088f2f3774082b936ee9f2335eff9
Source dataset
uspto-grants-1992_09
Patent number
US05145854

Reaction notes

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