Formaldehyde → (7-Methoxy-2,3-dihydrobenzo[f][1,4]thiazepin-4(5H)-yl)(morpholino)methanone

HRID 1917071Notes

Reaction equation

HRID 1917071 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]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])=[CH:5][CH:4]=1.C=O.[C:23]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]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])[CH2:23][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 17744820N-(2-(4-Methoxyphenylthio)ethyl)morpholine-4-carboxamide

Product 1

HCID 57864674(7-Methoxy-2,3-dihydrobenzo[f][1,4]thiazepin-4(5H)-yl)(morpholino)methanoneYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of compound 16 (100 mg), paraformaldehyde (110 mg), p-toluenesulfonic acid (60 mg) in benzene (5 mL) was stirred at 70-75° C. for 14 h. The reaction solution was filtrated, washed with sat. NaHCO3 and concentrated to give crude title product 17 in an estimated yield of ˜50% by TLC and NMR. Chromatography on SiO2 (CH2Cl2/EtOAc 10:1) provided pure sample for confirmation of the structure.

Workup

  1. filtrationThe reaction solution was filtrated
  2. washwashed with sat. NaHCO3
  3. concentrationconcentrated
  4. customto give crude title product 17 in an estimated yield of ˜50% by TLC and NMR
  5. customChromatography on SiO2 (CH2Cl2/EtOAc 10:1) provided pure sample for confirmation of the structure

Sources & evidence

ORD record
ord-8f95687f9eef40c387228e9cc72c858f
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

Loading…