Methylamine → HCID 18322369, compound

HRID 1688073Notes

Reaction equation

HRID 1688073 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[S:4][C:3]=1[C:11]([O-:13])=O.C[Al](C)C.[CH3:18][NH2:19]>C(Cl)Cl>[CH3:18][NH:19][C:11]([C:3]1[S:4][C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:6][C:2]=1[NH2:1])=[O:13]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7021228HCID 7021228, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 18322369HCID 18322369, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon, 3-amino-5-tert-butyl-thiophene-2-carboxylate (2.13 g, 10 mmol) was added to a premixed (15 minutes) methylene chloride (50 mL) solution of trimethylaluminum (5.0 mL, 2.0 M in hexanes) and methylamine (5.0 mL, 2.0 M in THF). The mixture solution was stirred at room temperature for 10 minutes and heated at 41° C. for 3 days. The mixture was cooled and carefully quenched with dilute HCl followed by extraction with methylene chloride. The organic phase was dried over sodium sulfate and concentrated. Column chromatography (hexanes/ethyl acetate) gave 0.3 g of 3-amino-5-tert-butyl-thiophene-2-carboxylic acid methylamide in 14% yield: 1H NMR (300 MHz, CDCl3) δ 6.44 (s, 1H), 5.6 (br, 2H), 5.4 (br, 1H), 3.02 (d, 3H), 1.44 (s, 9H); MS (m/e): 212.9 (M+1).

Workup

  1. temperatureheated at 41° C. for 3 days
  2. temperatureThe mixture was cooled
  3. customcarefully quenched with dilute HCl
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0a13e080e857418e99616a0f99a5ad84
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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