Methyl Thioglycolate → Methyl 3-amino-5-(3-chlorophenyl)thiophene-2-carboxylate

HRID 843575Notes

Reaction equation

HRID 843575 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].C[O-].[Na+].Cl[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)=[CH:12][C:13]#[N:14]>CO>[CH3:6][O:5][C:1]([C:2]1[S:3][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:12][C:13]=1[NH2:14])=[O:4]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 10942334Sodium MethoxideHCID 537586613-Chloro-3-(3-chlorophenyl)-2-propenenitrile

Product 1

HCID 11994772Methyl 3-amino-5-(3-chlorophenyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium pellets were slowly added to methanol solution to form NaOMe in situ, then methyl thioglycolate was added over a period of 20 minutes to the methanol solution. A solution of 3-Chloro-3-(3-chloro-phenyl)-acrylonitrile in methanol was added slowly and was brought to reflux for 1 hour. The reaction mixture was cooled to room temperature and methanol was concentrated to 100 mL and 200 mL of water was added, stirred for 30 min and the yellow precipitate was collected and washed with water several times to yield a yellow crystalline compound, mp 92-95° C. 1H NMR (DMSO-d6) δ1.60 (s, 6H), 7.30 (d, 1H, J=8.41 Hz), 7.41 (d, 1H, J=8.41 Hz), 10.47 (s, 1H); MS (+APCI) m/z 213(M+H); Anal. Calc. For C9H9ClN2O2: C, 50.84; H, 4.27; N, 13.17. Found: C, 50.99; H, 4.28; N, 12.98.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationmethanol was concentrated to 100 mL and 200 mL of water
  3. additionwas added
  4. customthe yellow precipitate was collected
  5. washwashed with water several times
  6. customto yield a yellow crystalline compound, mp 92-95° C

Sources & evidence

ORD record
ord-c3c0882bf19f407cbc8fd353399c7906
Source dataset
uspto-grants-2002_04
Patent number
US06380178B1

Reaction notes

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