O-Phenylenediamine → HCID 89418652, compound

HRID 2274531Notes

Reaction equation

HRID 2274531 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[F:9][C:10]([F:18])([F:17])[CH:11]([OH:16])[C:12](F)(F)F>>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][CH2:12][C@@H:11]([OH:16])[C:10]([F:18])([F:17])[F:9]

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 135291,1,1,3,3,3-Hexafluoro-2-propanol

Product 1

HCID 89418652HCID 89418652, compoundYield 66.2%

Procedure

Benzene-1,2-diamine (4.83 g, 44.6 mmol) was dissolved in hexafluoroisopropanol (9.37 mL, 89 mmol), (R)-trifluoromethylepoxide (0.769 mL, 8.92 mmol) was added, and the resulting reaction mixture was stirred at room temperature for 4 hours. The solution was concentrated and purified on a silica gel column with a 0-100% EtOAc/Hexanes gradient in a 100 g cartridge. (R)-3-[(2-aminophenyl)amino]-1,1,1-trifluoropropan-2-ol (1.30 g, 5.90 mmol) was obtained in 66.2% yield. 1H NMR (400 MHz, CDCl3) 83.32 (dd, J=13.4, 8.3 Hz, 1H), 3.55 (dd, J=13.5, 3.3 Hz, 1H), 3.55 (bs, 3H), 4.22 (m, 1H), 6.71 (d, J=7.7 Hz, 1H), 6.79 (m, 2H), 6.87 (d, d, J=7.7, 2.2 Hz, 1H). MS m/z=221.00

Workup

  1. addition(R)-trifluoromethylepoxide (0.769 mL, 8.92 mmol) was added
  2. customthe resulting reaction mixture
  3. concentrationThe solution was concentrated
  4. custompurified on a silica gel column with a 0-100% EtOAc/Hexanes gradient in a 100 g cartridge

Sources & evidence

ORD record
ord-db1a5361e3c84c1587508d8adcf2edb1
Source dataset
uspto-grants-2015_09
Patent number
US09126976B2

Reaction notes

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