Dimethylformamide dimethyl acetal → Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate

HRID 1916343Notes

Reaction equation

HRID 1916343 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>CCO>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]([C:14]([O:16][CH3:17])=[O:15])=[C:2]([N:1]=[CH:20][N:21]([CH3:23])[CH3:22])[CH:6]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Product 1

HCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared following the procedure described in WO2003033476. Condensation of 2.00 g of methyl 3-amino-5-(4-chlorophenyl)-thiophene-2-carboxylate with dimethylformamide dimethyl acetal for 3 hr in refluxing EtOH yielded 2.52 g (100%) after removal of the volatiles under vacuum. 1H NMR (CDCl3) δ 3.06 (s, 3H), 3.08 (s, 3H), 3.81 (s, 3H), 6.98 (s, 1H), 7.35 (d, J=8.79 Hz, 2H), 7.53 (d, J=8.24 Hz, 2H), 7.69 (s, 1H); 13C NMR (CDCl3) δ 34.31, 40.26, 51.44, 112.43, 122.28, 126.95, 129.09, 132.18, 134.45, 145.79, 156.09, 159.16, 163.22; HPLC (Method #1): 2.45 min retention time; MS (ES): m/z 323 [M+H]+.

Workup

  1. customyielded 2.52 g (100%)
  2. customafter removal of the volatiles under vacuum
  3. custom2.45 min retention time

Sources & evidence

ORD record
ord-7cf459a04d8f4fe9841341ad687c046b
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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