2-Amino-4-(methylsulfonyl)phenol → HCID 4594979, compound

HRID 1644384Notes

Reaction equation

HRID 1644384 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH2:12])[CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:19][C:20](Br)=[O:21]>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:19][C:20](=[O:21])[NH:12][C:7]=2[CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 73822-Amino-4-(methylsulfonyl)phenol2×HCID 61147Bromoacetyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 4594979HCID 4594979, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-Methylsulfonyl-2-aminophenol (Intermediate 102) (690 mg, 3.68 mmol) was dissolved in chloroform (30 mL) and saturated sodium bicarbonate (20 mL). The biphasic reaction mixture was cooled to 0° C. and bromoacetyl bromide (889 mg, 4.42 mmol) was added dropwise. The reaction was stirred overnight at room temperature. The layers were separated and the aqueous layer was filtered to yield the desired product as a solid, 280 mg (33%).

Workup

  1. customThe biphasic reaction mixture
  2. customThe layers were separated
  3. filtrationthe aqueous layer was filtered

Sources & evidence

ORD record
ord-a647522f9df145b9ad2a8bb1c34bf44b
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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