Formaldehyde → Methyl 4-chloro-3-(dimethylamino)benzo[b]thiophene-2-carboxylate

HRID 2226869Notes

Reaction equation

HRID 2226869 reaction equation
N[C:2]1[C:3]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C=O.[C:18]([BH3-])#[N:19].[Na+].[C:22](=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O>[Cl:15][C:14]1[C:3]2[C:2]([N:19]([CH3:18])[CH3:22])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[S:5][C:4]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 2818443Methyl 3-amino-4-chloro-1-benzothiophene-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18963790Methyl 4-chloro-3-(dimethylamino)benzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3-amino-4-chlorobenzo[b]thiophene-2-carboxylate (1.7 g, 7.0 mmol) [Beck J. R., supra] and paraformaldehyde (2.0 g, 67 mmol) in 45 mL of acetic acid is treated in portions with sodium cyanoborohydride (2.0 g, 32 mmol). The mixture is stirred at room temperature for 24 hours, then diluted cautiously with 250 g of ice and water. Solid sodium carbonate is added until the mixture is slightly basic. After extraction with ethyl acetate, the combined organic layers are washed with brine, then dried (anhydrous sodium sulfate), and evaporated to provide methyl 4-chloro-3-(dimethylamino)benzo[b]thiophene-2-carboxylate as an oil.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-c22f4b6d166f4ad583e4c3b8f6b48483
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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