Potassium Carbonate → HCID 66877166, compound

HRID 631450Notes

Reaction equation

HRID 631450 reaction equation
[CH3:1][O:2][C:3]([CH3:19])([CH3:18])[CH2:4][CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].C(=O)([O-])[O-].[K+].[K+].Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>O1CCCC1>[CH3:1][O:2][C:3]([CH3:19])([CH3:18])[CH2:4][CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:27](=[O:28])[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:9][C:8]=1[C:14]([F:16])([F:15])[F:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 6485753HCID 6485753, compound

Product 1

HCID 66877166HCID 66877166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure described in Example 113B, 4-(3-methoxy-3-methylbutoxy)-3-(trifluoromethyl)aniline (490 mg, 1.77 mmoles) was dissolved in 20 mL of dry tetrahydrofuran. To this solution was added potassium carbonate (318 mg, 2.30 mmoles) followed by phenyl chloroformate (360 mg, 2.30 mmoles). The mixture was stirred overnight at room temperature, then purified with silica gel chromatography (using a gradient of 0-30% ethyl acetate/hexanes) to afford phenyl 4-(3-methoxy-3-methylbutoxy)-3-(trifluoromethyl)-phenylcarbamate as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.58 (m, 2H), 7.40 (m, 2H), 7.35-7.1 (m, 4H), 6.9 (m, 1H), 4.10 (m, 2H), 3.22 (s, 3H), 2.1 (m, 2H), 2.1 (m, 2H).

Workup

  1. custompurified with silica gel chromatography (

Sources & evidence

ORD record
ord-a5b8683855694e64897cc8f85e24d850
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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