Hydrochloric Acid → 5-(4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-nitrobenzyl phenylcarbamate

HRID 1690180Notes

Reaction equation

HRID 1690180 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:18]=[CH:19][C:20]([N+:25]([O-:27])=[O:26])=[C:21]([CH2:23][OH:24])[CH:22]=2)=[C:14]([CH2:30][CH2:31][CH3:32])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].N1C=CC=CC=1.[C:41]1([N:47]=[C:48]=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl>ClCCl.O>[C:41]1([NH:47][C:48](=[O:49])[O:24][CH2:23][C:21]2[CH:22]=[C:17]([O:16][C:15]3[CH:28]=[CH:29][C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:6])([F:5])[F:7])[C:2]([F:33])([F:34])[F:1])=[CH:13][C:14]=3[CH2:30][CH2:31][CH3:32])[CH:18]=[CH:19][C:20]=2[N+:25]([O-:27])=[O:26])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7672Phenyl isocyanateHCID 86639411(5-(4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-nitrophenyl) methanol

Product 1

HCID 866394125-(4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-nitrobenzyl phenylcarbamateYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-nitrophenyl) methanol (221 mg, 0.444 mmol) in dichloromethane (2.2 mL), pyridine (72 μL, 0.889 mmol) was added. Phenylisocyanate (97 μL, 0.889 mmol) was added thereto under ice-cold conditions, and the resultant mixture was stirred at room temperature overnight. The reaction solution was added with water and 5% aqueous solution of hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using preparative thin-layer chromatography (hexane/ethyl acetate). 5-(4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-nitrobenzyl phenylcarbamate (249 mg, yield 91%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-1195cd582e4748b7bae71a4945987a6d
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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