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

HRID 1934831Notes

Reaction equation

HRID 1934831 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-02d19583e2ca4609b89e8e5093a367a6
Source dataset
uspto-grants-2002_05
Patent number
US06384234B1

Reaction notes

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