Hydrochloric Acid → HCID 14880459, compound

HRID 1533977Notes

Reaction equation

HRID 1533977 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3S(C2C=CC(C)=CC=2)(=O)=O)=[O:10])=[CH:5][CH:4]=1.[C-]#N.[Na+].Cl>CS(C)=O>[NH:15]1[C:16]2[C:12](=[C:11]([C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)=[O:10])[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 14880458HCID 14880458, compound

Product 1

HCID 14880459HCID 14880459, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 56.1 g of the product of Step C, 66.16 g of sodium cyanide and 370 ml of dimethylsulfoxide was heated for 16 hours at 140° C. and then the solution was allowed to return to ambient temperature. 1500 ml of 2N hydrochloric acid were added and extraction was done with sulfuric ether. The extracts were concentrated to dryness under reduced pressure and the 70.4 g residue were chromatographed on silica (eluant: methylene chloride - ethyl acetate (85-15) to obtain 20.1 g of the desired product melting at 177° C. which was used as is for the following step. After chromatography on silica of 5.5 g of the above product (eluant: ethyl acetate - n-hexane (4-6)) and crystallization of the residue from ethyl acetate - n-hexane, 3.96 g of pure product melting at 177° C. were obtained.

Workup

  1. customto return to ambient temperature
  2. extractionextraction
  3. concentrationThe extracts were concentrated to dryness under reduced pressure
  4. customthe 70.4 g residue were chromatographed on silica (eluant

Sources & evidence

ORD record
ord-3b2200c2b80d4a7bbc701e7c548d8348
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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