4-Aminophenol → HCID 11367402, compound

HRID 1474513Notes

Reaction equation

HRID 1474513 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[SH:9][CH2:10][C:11](O)=[O:12]>Cl>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:11](=[O:12])[CH2:10][SH:9])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 1133Thioglycolic Acid

Product 1

HCID 11367402HCID 11367402, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-aminophenol (4.0 g, 36.7 mmol) and mercaptoacetic acid (2.93 g, 38.5 mmol) under an atmosphere of carbon dioxide was heated to reflux (oil bath temperature ˜120° C.) for 4 hours. The mixture was cooled and diluted with 2 N hydrochloric acid (˜100 mL). A purple solid, 1.3 g, was collected by filtration and washed with water. The product was purified by flash chromatography, on silica gel, eluted with 5 to 10% methanol in DCM, to give a colorless solid, 1.03 g (15%). MS m/z 184 (MH+). 1H NMR(DMSO-d6) δ 2.08 (t, 1H), 3.24 (s, 2H), 6.70 (d, 2H), 7.35 (d, 2H), 9.21 (br s, 1H) and 9.83 (s, 1H). Anal. calcd for C8H9NO2S: C, 52.44; H, 4.95; N, 7.64. Found: C, 52.57; H, 4.95; N, 7.40.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. filtrationA purple solid, 1.3 g, was collected by filtration
  4. washwashed with water
  5. customThe product was purified by flash chromatography, on silica gel
  6. washeluted with 5 to 10% methanol in DCM
  7. customto give a colorless solid, 1.03 g (15%)

Sources & evidence

ORD record
ord-84e27572ff3f4613ad7270c561ae832c
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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