1,3-Propanediol → HCID 12926523, compound

HRID 851111Notes

Reaction equation

HRID 851111 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].Br[C:9]1[CH:10]=[C:11]([CH2:14][N:15]([CH3:17])[CH3:16])[S:12][CH:13]=1>[Cu]=O.[I-].[Na+].Cl>[CH3:16][N:15]([CH2:14][C:11]1[S:12][CH:13]=[C:9]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[CH:10]=1)[CH3:17]

Participants

7

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 223495551-(4-Bromothiophen-2-yl)-N,N-dimethylmethanamine

Product 1

HCID 12926523HCID 12926523, compound

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 14829Copper oxideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1,3-propanediol (20 ml) and sodium hydride (1 g) was stirred at 80° for 1 h. Copper (II) oxide (1.3 g), sodium iodide (0.05 g) and 4-bromo-N,N-dimethyl-2-thiophenemethanamine (5 g) were added and heating was continued for 2 days. Dilute hydrochloric acid (60 ml) was added and the aqueous solution was washed with diethyl ether (50 ml), basified with aqueous sodium hydroxide and extracted with chloroform (200 ml). The organic extract was distilled to give the title compound (1.7 g) as an off-white wax. m.p. 32°-4°

Workup

  1. temperatureheating
  2. waitwas continued for 2 days
  3. washthe aqueous solution was washed with diethyl ether (50 ml)
  4. extractionextracted with chloroform (200 ml)
  5. extractionThe organic extract
  6. distillationwas distilled

Sources & evidence

ORD record
ord-ed2e9eff1d6143cfba24f68d2cc6c020
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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