Water → HCID 22346949, compound

HRID 2056111Notes

Reaction equation

HRID 2056111 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=S)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[OH:19].O=O.[K+].O>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:19][C:13]3[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72652-Amino-4-chlorophenolHCID 161334-Bromophenyl isothiocyanateHCID 6154112030-88-5

Product 1

HCID 22346949HCID 22346949, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Bromophenyl isothiocyanate (3.639 g, 17.00 mmol) was added to a solution of 2-amino-4-chlorophenol (2.441 g, 17.00 mmol) in acetonitrile (20 mL) and the reaction was stirred at room temperature for 2 h. The resulting brown solution was then added dropwise, via a dropping funnel, to a suspension of potassium superoxide (6.04 g, 85.0 mmol) in acetonitrile (20 mL) pre-cooled to 0° C. in an ice bath. After 20 minutes the initial exotherm had subsided and the reaction was allowed to warm to room temperature for 40 minutes. Water (120 mL) was added dropwise and the resulting off-white solid was collected by filtration, washed with additional water (60 mL) and dried overnight on a lyophilizer to afford N2-(4-bromophenyl)-5-chloro-1,3-benzoxazol-2-amine as an off-white solid (4.06 g, 74%);

Workup

  1. temperaturepre-cooled to 0° C. in an ice bath
  2. waitAfter 20 minutes the initial exotherm had subsided
  3. temperatureto warm to room temperature for 40 minutes
  4. filtrationthe resulting off-white solid was collected by filtration
  5. washwashed with additional water (60 mL)
  6. customdried overnight on a lyophilizer

Sources & evidence

ORD record
ord-764d4c8dc5fd406ab9321644546c71d1
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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