Hydrochloric Acid → 2-Amino-4-(phenylthio)phenol hydrochloride

HRID 2075263Notes

Reaction equation

HRID 2075263 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[CH:10][C:11]3[O:15]C=[N:13][C:12]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:17].O>CCO.C(Cl)Cl>[ClH:17].[NH2:13][C:12]1[CH:16]=[C:8]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][C:11]=1[OH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 225015745-(Phenylthio)benzo[d]oxazole

Product 1

HCID 670921602-Amino-4-(phenylthio)phenol hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(phenylthio)benzo[d]oxazole (1.04 g, 4.6 mmol) and conc. HCl (0.97 mL, 11 mmol) under nitrogen in 4.6 mL EtOH in a 50 mL rbf fitted with a water-cooled reflux condensor was placed in a 100° C. bath. After 2 h, the mixture was cooled, concentrated in vacuo and dried to give a yellow solid. The material was sonicated in 10 mL DCM, filtered, rinsing with DCM, and dried to give 2-amino-4-(phenylthio)phenol hydrochloride as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.72 (s, 1H), 8.75 (br. s., 1H), 7.28-7.35 (m, 2H), 7.12-7.25 (m, 5H), 6.99 (d, J=8.0 Hz, 1H), 4.32 (br. s., 2H).

Workup

  1. temperaturecooled
  2. temperaturereflux condensor
  3. customwas placed in a 100° C.
  4. temperaturethe mixture was cooled
  5. concentrationconcentrated in vacuo
  6. customdried
  7. customto give a yellow solid
  8. filtrationfiltered
  9. washrinsing with DCM
  10. customdried

Sources & evidence

ORD record
ord-b9c8984b691143648194098c920bc5fb
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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