Ammonia → HCID 21183144, compound

HRID 1386877Notes

Reaction equation

HRID 1386877 reaction equation
Cl[C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6].[NH3:16]>>[NH2:16][C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 21183181HCID 21183181, compound

Product 1

HCID 21183144HCID 21183144, compound

Conditions

Temperature
180 °C

Procedure

A mixture of 79.0 g (grams)(320 mmol (millimole)) of 3-chloro-2-methyl-4-methylsulfonylbenzoic acid, 1.0 g (12.6 mmol) of cupric oxide, and 500 mL (milliliter) of concentrated aqueous ammonia was heated at 180° C. for 17 hours in a stirred Parr reactor. The resulting dark mixture was concentrated by evaporation under reduced pressure. The residue was acidified with 2N aqueous hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The extract was filtered and concentrated by evaporation under reduced pressure. The solid residue was mixed with hexane, recovered by filtration, and dried to obtain 50.0 g (68 percent of theory) of the title acid compound as a light tan powder melting at 197-198° C.

Workup

  1. concentrationThe resulting dark mixture was concentrated by evaporation under reduced pressure
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. filtrationThe extract was filtered
  4. concentrationconcentrated by evaporation under reduced pressure
  5. additionThe solid residue was mixed with hexane
  6. filtrationrecovered by filtration
  7. customdried

Sources & evidence

ORD record
ord-4b57fee522b34121ab21f471d4a83f7d
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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