Pyridine → HCID 20379297, compound

HRID 2051614Notes

Reaction equation

HRID 2051614 reaction equation
C(O)(=O)C(O)=O.[NH2:7][CH2:8][CH:9]([OH:11])[CH3:10].N1C=CC=CC=1.[C:18](=[S:20])=[S:19].[CH3:21]I>C(N(CC)CC)C>[OH:11][CH:9]([CH3:10])[CH2:8][NH:7][C:18](=[S:20])[S:19][CH3:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 20379310HCID 20379310, compound

Product 1

HCID 20379297HCID 20379297, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

40 G (0.242 mmole) of 1-amino-2-propanol oxalate was suspended in 180 ml. of pyridine and 101 g. of triethylamine was added. The mixture was stirred mechanically for 1 hour, there cooled to 0° and 38 g. of carbon disulfide (0.5 mole) was added dropwise. After 2 hours at 0° C., 36 g. of methyl iodide (0.254 mole) was added dropwise and almost all solids dissolved. The mixture was stored in a refrigerator overnight (0°-5° C.). The mixture was poured into 2.4 l. of 3 N H2SO4 and extracted with ether 3 times. The ether extracts were washed with water, 3 N H2SO4, water, aqueous NaHCO3 solution and water, dried over Na2SO4 and stripped down to 18.79 g. (47%) of oily methyl N-(2-hydroxypropyl) dithiocarbamate.

Workup

  1. temperaturethere cooled to 0°
  2. waitAfter 2 hours at 0° C.
  3. dissolutionalmost all solids dissolved
  4. customwas stored in a refrigerator overnight (0°-5° C.)
  5. additionThe mixture was poured into 2.4 l
  6. extractionof 3 N H2SO4 and extracted with ether 3 times
  7. washThe ether extracts were washed with water, 3 N H2SO4, water, aqueous NaHCO3 solution and water
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-7a31c22016964949b376e6e03db6b274
Source dataset
uspto-grants-1980_01
Patent number
US04181661

Reaction notes

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