Triethylamine → HCID 86585986, compound

HRID 1935636Notes

Reaction equation

HRID 1935636 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH:19]=[O:20])[CH:14]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]3)[CH2:5]1.C(N(CC)CC)C.[C:32](SCC)(=[S:34])[CH3:33]>CO>[CH3:22][C:21]([CH:14]1[CH2:13][C:12]2[C:16](=[CH:17][CH:18]=[C:10]([N:6]3[CH2:5][C@H:4]([CH2:3][NH:2][C:32](=[S:34])[CH3:33])[O:8][C:7]3=[O:9])[CH:11]=2)[N:15]1[CH:19]=[O:20])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 86585987HCID 86585987, compound

Product 1

HCID 86585986HCID 86585986, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The amine hydrochloride salt (200 mg, 0.566 mmol) prepared in Step 12 is stirred in a mixture of methanol (4 ml) and triethylamine (0.234 ml, 1.683 mmol). To this solution is added ethyl dithioacetate (0.08 ml, 0.70 mmol) and the mixture heated to reflux for 2 hours then allowed to cool. The precipitate is filtered to afford the thioamide as white needles (97 mg, 46%): mp 219-221° C. Anal: Calcd. for C19H25N3O3S: C, 60.78; H, 6.71; N, 11.19. Found: C, 60.63; H, 6.80; N, 11.12.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-869450fb6a184747905fa728d281a476
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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