Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 178525496, compound

HRID 2231934Notes

Reaction equation

HRID 2231934 reaction equation
[OH:1][C:2]1[NH:3][C:4]2C=CC=C[C:5]=2[N:6]=1.[C:11]([CH2:15][CH2:16][C:17](Cl)=[O:18])([O:13]C)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:11]([CH2:15][CH2:16][C:17]([C:5]1[NH:6][C:2]([OH:1])=[N:3][CH:4]=1)=[O:18])([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) ChlorideHCID 178517141HCID 178517141, compound

Product 1

HCID 178525496HCID 178525496, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Carbon disulfide (110 ml), 2-hydroxybenzimidazole (5 g) and 3-carbomethoxypropionyl chloride (5.6 g) are added to a flask containing aluminum chloride (25 g) under an atmosphere of nitrogen. The resulting suspension is refluxed for about 20 hours, quenched with ice cold hydrochloric acid (6N), stirred and filtered. The filtered solid is washed with water and dried in a vacuum oven, affording the desired compound as a solid, which is used in the next step without further purification, M.P. 295° C. (dec).

Workup

  1. temperatureThe resulting suspension is refluxed for about 20 hours
  2. customquenched with ice cold hydrochloric acid (6N)
  3. filtrationfiltered
  4. washThe filtered solid is washed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-fcdf2befe4cb41d2b17959c18ba67c43
Source dataset
uspto-grants-1988_11
Patent number
US04785101

Reaction notes

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