Hydrochloric Acid → 5-Chloro-2-((2-chloroacetyl)amino)benzoic acid

HRID 1899394Notes

Reaction equation

HRID 1899394 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][CH2:13][C:14](Cl)=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[Cl:12][CH2:13][C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 41798255-Chloro-2-((2-chloroacetyl)amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

12.5 g (73 mmol) of 2-amino-5-chlorobenzoic acid are initially introduced into 500 ml of acetonitrile and treated with 9.0 g (80 mmol) of chloroacetyl chloride with stirring, the temperature being kept at 20°-25° C. (ice-bath). 22 g (0.16 mol) of finely pulverized potassium carbonate are then introduced and the mixture is stirred overnight at room temperature. The batch is adjusted to pH 2 with dilute hydrochloric acid and the acetonitrile is stripped off on a rotary evaporator. The precipitate is filtered off with suction and washed well with water. The crude product is treated with sodium bicarbonate solution and stirred. Insoluble matter is filtered off with suction and the filtrate acidified with dilute hydrochloric acid to pH 2. The precipitated product is filtered off with suction and dried. Yield: 7 g (77.3% of theory) M.p.: 188° C.

Workup

  1. custombeing kept at 20°-25° C.
  2. stirringthe mixture is stirred overnight at room temperature
  3. customthe acetonitrile is stripped off on a rotary evaporator
  4. filtrationThe precipitate is filtered off with suction
  5. washwashed well with water
  6. additionThe crude product is treated with sodium bicarbonate solution
  7. stirringstirred
  8. filtrationInsoluble matter is filtered off with suction
  9. filtrationThe precipitated product is filtered off with suction
  10. customdried

Sources & evidence

ORD record
ord-a1de311ebc264719961cf4cbd214c1b8
Source dataset
uspto-grants-1996_11
Patent number
US05571921

Reaction notes

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