Triethylamine → N-cyclopropyl-2-(pyridine-3-carbothioamido)acetamide

HRID 515133Notes

Reaction equation

HRID 515133 reaction equation
CS[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[S:4].[NH2:11][CH2:12][C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14].C(N(CC)CC)C>CO.C(OCC)(=O)C>[CH:16]1([NH:15][C:13](=[O:14])[CH2:12][NH:11][C:3]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)=[S:4])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 49627272-amino-N-cyclopropylacetamideHCID 117450493-Pyridinecarbodithioic acid, methyl ester

Product 1

HCID 86704352N-cyclopropyl-2-(pyridine-3-carbothioamido)acetamideYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methylpyridine-3-carbodithioate (2.97 g, 17.52 mmol) in methanol (10 mL) was added a solution of 2-amino-N-cyclopropylacetamide (2 g, 17.52 mmol) (HCl salt) and triethylamine (3.55 g, 35.0 mmol). The mixture was stirred at room temperature for 1 hour and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-cyclopropyl-2-(pyridine-3-carbothioamido)acetamide as a yellow solid (3.60 g, 83%): mp 152-153° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H), 8.91 (ddd, J=7.0, 2.3, 0.7 Hz, 1H), 8.76-8.56 (m, 1H), 8.10 (m, 2H), 7.57-7.32 (m, 1H), 4.26 (m, 2H), 2.73-2.57 (m, 1H), 0.77-0.61 (m, 2H), 0.50-0.29 (m, 2H); ESIMS (m/z) 234 ([M−H]−).

Workup

  1. washwashed with saturated aqueous NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-033b01ce2be54b2e8886532a75e4469b
Source dataset
uspto-grants-2015_08
Patent number
US09108952B2

Reaction notes

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