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

HRID 1164800Notes

Reaction equation

HRID 1164800 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-8e26151d8df24270b7a05b2192b6388f
Source dataset
uspto-grants-1990_03
Patent number
US04906630

Reaction notes

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