Acetic Acid → HCID 13536198, compound

HRID 652428Notes

Reaction equation

HRID 652428 reaction equation
[C:1]([CH2:3][S:4][C:5]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:6]=1[O:7][CH2:8][C:9]#[N:10])#[N:2].C[O-].[Na+].C(O)(=O)C>CN(C)C=O>[NH2:10][C:9]1[CH2:8][O:7][C:6]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:5]=2[S:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13536199HCID 13536199, compound

Product 1

HCID 13536198HCID 13536198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 120 ml of N,N-dimethylformamide is dissolved 30 g of 2-cyanomethylthio-4-methoxyphenoxyacetonitrile, and 30 g of 28% sodium methoxide is added dropwise to the solution under ice-cooling and under a nitrogen gas stream with stirring, followed by stirring for 2 hours. The reaction mixture is poured in ice-cold water containing 12 g of acetic acid, and the precipitate is collected by filtration, washed with water and recrystallized from chloroform to give colorless prisms of 3-amino-7-methoxy-2H-1,5-benzoxathiepin-4-carbonitrile. Yield of 19.5 g, m.p. of 203°-205° C.

Workup

  1. additionis added dropwise to the solution under ice-
  2. temperaturecooling and under a nitrogen gas stream
  3. stirringby stirring for 2 hours
  4. filtrationthe precipitate is collected by filtration
  5. washwashed with water
  6. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-77657c8085ee4a31887826827e60fa8b
Source dataset
uspto-grants-1987_06
Patent number
US04672064

Reaction notes

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