Water → HCID 86657975, compound

HRID 2366805Notes

Reaction equation

HRID 2366805 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].O.[C:16](Cl)(=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.C(OCC)(=O)C>[OH:8][C:6]1[CH:7]=[C:2]([NH:1][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=[CH:4][C:5]=1[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 178185-Amino-2-methylphenolHCID 516892Sodium Bicarbonate

Product 1

HCID 86657975HCID 86657975, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-amino-2-methylphenol (39.6 g, 321 mmol) and sodium hydrogen carbonate (40.5 g, 482 mmol) in tetrahydrofuran (300 mL)/water (150 mL) was added dropwise benzyl chlorocarbonate (48.1 mL, 321 mmol) at 0° C. over 30 min, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL), and the obtained aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layer was washed with saturated brine (100 mL), and purified by silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure to give the title compound (83.1 g, quantitatively) as a pale-brown solid. The obtained compound was used for the next reaction without purification.

Workup

  1. washwashed with water (100 mL)
  2. extractionthe obtained aqueous layer was extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layer was washed with saturated brine (100 mL)
  4. custompurified by silica gel (ethyl acetate)
  5. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-028d21f5cc574c42b7dd66ff8797d369
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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