Sodium Hydroxide → N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432950Notes

Reaction equation

HRID 432950 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][Cl:13])(=[O:11])=[O:10])=[CH:6][C:5]([NH:14]C(=O)C)=[C:4]([F:18])[CH:3]=1.[OH-].[Na+]>Cl>[NH2:14][C:5]1[C:4]([F:18])=[CH:3][C:2]([Cl:1])=[C:7]([NH:8][S:9]([CH2:12][Cl:13])(=[O:11])=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10870764N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

Product 1

HCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

74.5 g of crude N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide (purity: 90%) was suspended in 355 mL of 6 N hydrochloric acid and heated to 95° C. After 1.5 hours the suspension turned into a solution. The mixture was cooled to room temperature and 90 mL of a NaOH solution (50%) was added (pH 3). The precipitated product was filtered and washed with water to yield, after drying, 62.8 g of the title compound as yellow crystals (purity: 86.4% by HPLC) which could be further purified by recrystallization as described above in Example 5.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitated product was filtered
  3. washwashed with water
  4. customto yield
  5. customafter drying
  6. custom62.8 g of the title compound as yellow crystals (purity: 86.4% by HPLC) which could be further purified by recrystallization

Sources & evidence

ORD record
ord-521012372ca04627aba230e2dccca369
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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