Hydrogen Bromide → HCID 59485630, compound

HRID 1972220Notes

Reaction equation

HRID 1972220 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[CH2:15][NH:16]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.Br>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 59485820HCID 59485820, compound

Product 1

HCID 59485630HCID 59485630, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-(4-(4-chlorophenoxy)phenylamino)-2-(3-(trifluoromethyl)phenyl)ethyl)-4-methylbenzenesulfonamide (358 mg, 0.638 mmol) and phenol (180 mg, 1.92 mmol) in 30 wt % HBr in acetic acid (3.5 mL) is heated at 80° C. for 2 h. After cooling down to room temperature, most of the solvent is removed under vacuo. The residue is then quenched with cold saturated NaHCO3 aqueous solution (40 mL) and extracted with EtOAc (3×20 mL). The combined organic layer is concentrated and purified by reverse phase HPLC to provide N1-(4-(4-chlorophenoxy)phenyl)-1-(3-(trifluoromethyl)phenyl)ethane-1,2-diamine (128 mg, 49% yield) as a light yellow oil-like product.

Workup

  1. customis removed under vacuo
  2. customThe residue is then quenched with cold saturated NaHCO3 aqueous solution (40 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. concentrationThe combined organic layer is concentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-cc2e6cb801f44a05903de912b1b327ec
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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