O-Phenylenediamine → HCID 1486498, compound

HRID 537318Notes

Reaction equation

HRID 537318 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1([S:15][CH2:16][C:17](O)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>Cl>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:17]=1[CH2:16][S:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 59541(Phenylthio)acetic acid

Product 1

HCID 1486498HCID 1486498, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 100 mL flask fitted with a stir-bar and condenser was charged with 1,2-phenylenediamine (2.88 g, 26.6 mmol), (phenylthio)acetic acid (4.00 g, 26.6 mmol), and 4M HCl (40 mL). The resultant suspension was heated in a 130° C. bath 48 hr. The mixture was cooled and concentrated in vacuo to a brown syrup. The syrup was taken up in EtOAc (100 mL) and washed with saturated NaHCO3 (2×75 mL) and brine (50 mL). The solution was filtered through phase separation paper and concentrated in vacuo to a tan solid. The crude solid was triturated with hexanes:EtOAc 6:1 (50 mL), filtered, pressed with rubber dam, and rinsed with hexanes:EtOAc 4:1 (2×10 mL). The material was dried to give 4.4 g of 68 as a tan solid (77%). 1H NMR (300 MHz, CDCl3): δ 11.7 (bs, 1H), 7.7-7.4 (m, 2H), 7.4-6.9 (m, 7H), 4.4 (s, 2H) ppm. HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 99% with retention time of 4.0 min.

Workup

  1. customA 100 mL flask fitted with a stir-bar and condenser
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo to a brown syrup
  4. washwashed with saturated NaHCO3 (2×75 mL) and brine (50 mL)
  5. filtrationThe solution was filtered through phase separation paper
  6. concentrationconcentrated in vacuo to a tan solid
  7. customThe crude solid was triturated with hexanes:EtOAc 6:1 (50 mL)
  8. filtrationfiltered
  9. washrinsed with hexanes:EtOAc 4:1 (2×10 mL)
  10. customThe material was dried

Sources & evidence

ORD record
ord-54c0af4ffad7413dbb8afd2aa9e4341d
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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