Ammonia → HCID 19831102, compound

HRID 1493228Notes

Reaction equation

HRID 1493228 reaction equation
[N:1]1([CH:6]([C:10]2[S:14][C:13]([CH2:15]O)=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.Cl.[C-:22]#[N:23].[Na+].N>CS(C)=O>[N:1]1([CH:6]([C:10]2[S:14][C:13]([CH2:15][C:22]#[N:23])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 19831112HCID 19831112, compound

Product 1

HCID 19831102HCID 19831102, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.2 g of the alcohol of example 8 is converted, with thionyl chloride (2 hours at room temperature, concentration by evaporation, redistillation three times with toluene) into the hydrochloride of the chloromethyl compound, which is dissolved in 2 ml of dimethyl sulfoxide and is mixed with 0.2 g of sodium cyanide. After stirring for 20 hours, it is added to dilute ammonia solution, extracted with ethyl acetate and the ethyl acetate extract is dried and concentrated by evaporation. After distillation on a bulb tube, the title compound is obtained as oil. Boiling point: 210°-230° C./0.03 mbar.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe ethyl acetate extract
  3. customis dried
  4. concentrationconcentrated by evaporation
  5. distillationAfter distillation on a bulb tube

Sources & evidence

ORD record
ord-c9a94f940ac54ab49626334560d815d5
Source dataset
uspto-grants-1991_06
Patent number
US05021434

Reaction notes

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