Hydrochloric Acid → HCID 19895651, compound

HRID 892597Notes

Reaction equation

HRID 892597 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=3[O:12][C:11]([CH3:22])([CH3:21])[CH:10]=2)=[C:5]([O:23]C)[CH:4]=1)#N.C[S-].[Na+].O.Cl.[CH3:30][N:31](C)C=O>C(OCC)C>[C:30]([C:8]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([C:9]2[C:14]3[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=3[O:12][C:11]([CH3:21])([CH3:22])[CH:10]=2)[CH:7]=1)#[N:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 19895617HCID 19895617, compound

Product 1

HCID 19895651HCID 19895651, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.58 g of 4-(4-cyano-2-methoxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and 1.05 g of sodium methanethiolate were heated at 100° C. for 20 minutes in 15 ml of dimethylformamide. The mixture was allowed to cool to room temperature and then poured into water and diethyl ether. The aqueous phase was acidified with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed three times with water, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (2:3) for the elution. After o recrystallization of the product from toluene there were obtained 1,1 g of 4-(5-cyano-2-hydroxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile of melting point 213°-215° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed three times with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution
  8. customAfter o recrystallization of the product from toluene

Sources & evidence

ORD record
ord-1dfa3f3d72f04ddfa58243962f55eba2
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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