Hydrochloric Acid → N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432964Notes

Reaction equation

HRID 432964 reaction equation
[NH2:1][C:2]1[C:3]([F:18])=[CH:4][C:5]([Cl:17])=[C:6]([N:8]([S:12]([CH2:15][Cl:16])(=[O:14])=[O:13])C(=O)C)[CH:7]=1.Cl>C(O)C.[OH-].[Na+]>[NH2:1][C:2]1[C:3]([F:18])=[CH:4][C:5]([Cl:17])=[C:6]([NH:8][S:12]([CH2:15][Cl:16])(=[O:14])=[O:13])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18760836N-(5-amino-2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide

Product 1

HCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamideYield 92.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

3 g (0.0095 mol) of N-(5-amino-2-chloro-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide were dissolved in 30 mL of ethanol and 30 mL of 25% sodium hydroxide solution. The mixture was stirred for 3 hours at 50° C. and then cooled to room temperature. 6 N hydrochloric acid was added with stirring and cooling until the solution had a pH of 5-6. The suspension was further cooled to 0-5° C., filtered, washed with water and dried to yield 2.4 g (92%) of the title compound as a solid melting at 103.5-105.5° C. Recrystallization from toluene raised the melting point to 105-106° C.

Workup

  1. temperaturecooled to room temperature
  2. stirringwith stirring
  3. temperaturecooling until the solution
  4. temperatureThe suspension was further cooled to 0-5° C.
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ec5998f511cd45679a2bca963534d155
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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