Potassium Carbonate → HCID 66877166, compound

HRID 1917895Notes

Reaction equation

HRID 1917895 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-a65975191f19460da6c8d045f5e23e15
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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