Formaldehyde → 5-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol

HRID 851110Notes

Reaction equation

HRID 851110 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH3:9].C=O.[C:13](=O)([O-])[O-:14].[Na+].[Na+].[OH-].[Na+]>Cl.C(O)(=O)C>[CH3:9][C:5]1[S:6][C:7]([CH2:13][OH:14])=[CH:8][C:4]=1[CH2:3][N:2]([CH3:10])[CH3:1]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 10374728N,N,2-Trimethyl-3-thiophenemethanamine

Product 1

HCID 129265265-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N,N,2-trimethyl-3-thiophenemethanamine (6.1 g), paraformaldehyde (3.0 g) in conc. hydrochloric acid (20 ml) and acetic acid (45 ml) was stirred at 0° to 5° C. for 1 hour, and at 8° for 72 hours. The mixture was added to an ice-cold, saturated solution of sodium carbonate. Aqueous 5 M sodium hydroxide was added and the mixture was stirred for 20 hours. The solution was extracted with chloroform and the organic extract was washed with dilute sodium hydroxide and saturated brine, dried and evaporated to leave an oil. This residue was distilled to give the title compound (6 g) as a pale yellow oil b.p. 120°/0.1 mm. The oxalate salt was formed in ethanol and ethyl acetate m.p. 129°-131° C.

Workup

  1. waitat 8° for 72 hours
  2. stirringthe mixture was stirred for 20 hours
  3. extractionThe solution was extracted with chloroform
  4. extractionthe organic extract
  5. washwas washed with dilute sodium hydroxide and saturated brine
  6. customdried
  7. customevaporated
  8. customto leave an oil
  9. distillationThis residue was distilled

Sources & evidence

ORD record
ord-9a48d1d922884e64a9136201f00c4aab
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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