(4-Aminophenoxy)benzene → 6-Phenoxybenzo[d]thiazol-2-amine

HRID 359775Notes

Reaction equation

HRID 359775 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[O:5]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:14]2[CH:13]=[C:12]([O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 15666Ammonium thiocyanateHCID 24408Bromine

Product 1

HCID 23449966-Phenoxybenzo[d]thiazol-2-amineYield 65.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

20.5 g of ammonium thiocyanate were added to a solution of 25 g of 4-phenoxyaniline in 250 ml of acetic acid, and the mixture was stirred, whilst cooling. While the internal temperature was maintained at 12 to 18° C., 6.95 ml of bromine was added dropwise to the mixture. After completion of the dropwise addition, the mixture was stirred for 2 hours, after which the solvent was removed by evaporation under reduced pressure. 300ml of ethyl acetate and 200 ml of water were added to the residue, and the resulting mixture was neutralized with sodium bicarbonate. The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, and then dehydrated over anhydrous magnesium sulfate after which it was concentrated by evaporation under reduced pressure. The solid obtained was triturated in diisopropyl ether, and filtered to give 21.34 g of the title compound, melting at 171-172° C.

Workup

  1. temperaturewhilst cooling
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred for 2 hours
  4. customafter which the solvent was removed by evaporation under reduced pressure
  5. addition300ml of ethyl acetate and 200 ml of water were added to the residue
  6. customThe ethyl acetate layer was separated
  7. washwashed with an aqueous solution of sodium chloride
  8. concentrationwas concentrated by evaporation under reduced pressure
  9. customThe solid obtained
  10. customwas triturated in diisopropyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-eb29142027c147c19c01b94e4d842bec
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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