Formaldehyde → 7-Methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carbaldehyde

HRID 1917069Notes

Reaction equation

HRID 1917069 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][CH:13]=[O:14])=[CH:5][CH:4]=1.C=O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[S:9][CH2:10][CH2:11][N:12]([CH:13]=[O:14])[CH2:17][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 57864671N-(2-(4-Methoxyphenylthio)ethyl)formamide

Product 1

HCID 578646727-Methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carbaldehydeYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of compound 14 (100 mg), paraformaldehyde (100 mg), p-toluenesulfonic acid (60 mg) in benzene (5 mL) was stirred at 70-75° C. for 2 days. Filtration, washing with sat. NaHCO3 and concentration gave crude product 15 in an estimated yield of ˜70% by TLC and NMR.

Workup

  1. filtrationFiltration
  2. washwashing with sat. NaHCO3 and concentration

Sources & evidence

ORD record
ord-8099296a4cc14145b34d3b0779eb80df
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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