Dimethylformamide dimethyl acetal → 3-(Dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester

HRID 1468991Notes

Reaction equation

HRID 1468991 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:10][O:9][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[N:1]=[CH:13][N:14]([CH3:16])[CH3:15])=[O:8]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 672186663-(Dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl esterYield 95%

Procedure

A mixture of methyl 3-amino-2-thiophenecarboxylate (1.572 g, 10 mmol) in 5 ml of N,N-dimethylformamide dimethyl acetal (DMF-DMA) was heated at reflux for 2 h and then allowed to cool to room temperature. The resulting mixture was evaporated to give 2.019 g (95%) of orange residue. 1H NMR (400 MHz, DMSO-d6) δ 7.75 (s, 1H), 7.63 (d, J=5.6 Hz, 1H), 6.81 (d, J=5.2 Hz, 1H), 3.67 (m, 3H), 3.00 (s, 3H), 2.93 (s, 3H); LC-MS (ESI) m/z 213.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe resulting mixture was evaporated

Sources & evidence

ORD record
ord-a8750d18ebe149ac8f2735487fd986b5
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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