Formaldehyde → HCID 178503091, compound

HRID 325638Notes

Reaction equation

HRID 325638 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:14][S:15]([O-:17])=[O:16].[Na+].C=O.[CH2:21](N(CC)CC)C>O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:14][S:15]([CH3:21])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 2733271Sodium methanesulfinateHCID 178503089HCID 178503089, compound

Product 1

HCID 178503091HCID 178503091, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-7-methylthioquinoline (4.2 g.), sodium methanesulphinate (8.2 g.), aqueous formaldehyde (37%, 9.0 ml.), triethylamine (2.85 ml.), industrial methylated spirit (130 ml.) and water (50 ml.) was stirred and boiled under reflux for 96 hours. The mixture was cooled to room temperature and filtered. The residue was washed with hot industrial methylated spirit to give the novel compound 4-hydroxy-3-methylsulphonylmethyl-7-methylthioquinoline, m.p. 290°-292°.

Workup

  1. temperatureunder reflux for 96 hours
  2. filtrationfiltered
  3. washThe residue was washed with hot industrial methylated spirit

Sources & evidence

ORD record
ord-30f020f80215497ea677c84fb96e9e84
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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