Formaldehyde → Methyl 7-methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carboxylate

HRID 1917063Notes

Reaction equation

HRID 1917063 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:5][CH:4]=1.C=O.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:9][CH2:10][CH2:11][N:12]([C:13]([O:14][CH3:15])=[O:16])[CH2:19][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 57864658Methyl 2-(4-methoxyphenylthio)ethylcarbamate

Product 1

HCID 57864656Methyl 7-methoxy-2,3-dihydrobenzo[f][1,4]thiazepine-4(5H)-carboxylateYield 208.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of compound 7 (95 mg), paraformaldehyde (95 mg, excess), p-toluenesulfonic acid (30 mg) in benzene (4 mL) was stirred at 60° C. overnight. Analysis by TLC showed a new spot and the complete disappearance of the starting material. Filtration, followed by concentration and chromatography on SiO2 gave 92 mg of pure product 8. Yield: 95%.

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration and chromatography on SiO2

Sources & evidence

ORD record
ord-54c61a7275e34b959877eacc7f458d2c
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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