Sodium Carbonate → HCID 18697891, compound

HRID 2289579Notes

Reaction equation

HRID 2289579 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[CH2:29][OH:30].O.O1CCCC1>O.C(OCC)C>[CH2:11]([O:10][C:8]([NH:18][C:19]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:20]=1[CH2:29][OH:30])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 18697900HCID 18697900, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 18697891HCID 18697891, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

1H-NMR (CDCl3): δ 1.65 (1H, brs), 4.35 (2H, brs), 4.71 (2H, s), 6.95 (1H, dd), 6.91 (1H, s), 7.16 (1H, d). (c) Sodium carbonate (2.5 g, 23.6 mmol) and benzyl chloroformate (3.3 ml, 23.1 mmol) were added to a solution of 2-amino-4-trifluoromethyl-1-hydroxymethylbenzene (4.08 g, 21.3 mmol), prepared in the step (b), in a water-tetrahydrofuran 1:1 solution (40 ml), and the mixture was stirred at room temperature for 21 hr. Diethyl ether and water were added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 2-benzyloxycarbonylamino-4-trifluoromethyl-1-hydroxymethylbenzene (6.85 g, 99%) as a white solid.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-311da96c72ae4af3a549a31429283db1
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

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