Carbon Disulfide → HCID 20376214, compound

HRID 2052556Notes

Reaction equation

HRID 2052556 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[OH:4].[C:15](=[S:17])=[S:16].C(N(CC)CC)C.C(Cl)C1C=CC=CC=1>N1C=CC=CC=1>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:15](=[S:16])[SH:17])[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 38639783,4-Dimethoxyphenylethanolamine

Product 1

HCID 20376214HCID 20376214, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10 mmol of 2-amino-1-(3,4-dimethoxyphenyl)-ethanol is dissolved in 6 ml. of pyridine and, under cooling to 0°, combined dropwise with 11 mmol of carbon disulfide in 10 mmol of triethylamine. During this step, the temperature rises greatly. The mixture is agitated for one hour at 0° and then, at the same temperature, 10 mmol of benzyl choride is added dropwise thereto. After agitation overnight at 0°, the batch is taken up in 40 ml. of 3 N sulfuric acid and extracted three times with respectively 50 ml. of chloroform. The combined chloroform phases are washed in succession with sodium bicarbonate and water, dried, filtered, and concentrated. The residue, which crystallizes spontaneously, is recrystallized from benzene and ethyl acetate, thus obtaining in a quantitative yield the benzyl ester of [2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-dithiocarbamic acid, m.p. 130°-132°.

Workup

  1. waitAfter agitation overnight at 0°
  2. extractionof 3 N sulfuric acid and extracted three times with respectively 50 ml
  3. washThe combined chloroform phases are washed in succession with sodium bicarbonate and water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue, which crystallizes spontaneously
  8. customis recrystallized from benzene and ethyl acetate

Sources & evidence

ORD record
ord-ba3230286d04441d82324bedea8f247e
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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