Potassium Carbonate → (4-Amino-3-methylphenyl)-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester

HRID 602512Notes

Reaction equation

HRID 602512 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[C:9]([O:13][C:14](=[O:37])[N:15]([C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[C:29]([CH3:36])[CH:28]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[C:9]([O:13][C:14](=[O:37])[N:15]([C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[C:29]([CH3:36])[CH:28]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:19][CH:18]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 67267024(3-Methyl-4-nitrophenyl)-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester

Product 1

HCID 67266881(4-Amino-3-methylphenyl)-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl esterYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Na2S2O4 (3.00 g, 17.2 mmol) in water (20 mL) was added to a solution of (3-methyl-4-nitrophenyl)-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester (1.41 g, 3.44 mmol) in tetrahydrofuran (20 mL), and the resulting mixture was stirred for 20 hours at +55° C. After cooling to room temperature, the water phase was saturated with potassium carbonate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate, solvents were evaporated, and the residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield the title compound as a white solid (1.09 g, 83%).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate, solvents
  4. customwere evaporated
  5. customthe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-ee0b1f2ed16e461497942ae7ec8392c3
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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