Potassium Iodide → methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

HRID 1684321Notes

Reaction equation

HRID 1684321 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][C:10](=[O:13])[O:11][CH3:12])=[C:4]([F:14])[CH:3]=1.C1(C)C=CC(S(O[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:6][C:5]([NH:9][C:10](=[O:13])[O:11][CH3:12])=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateHCID 19042327methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

Product 1

HCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamateYield 93.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 10-L three-necked flask equipped with a mechanical stirrer and a Dimroth condenser was charged with methyl N-(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate (1.64 kg, 7.47 mol), cyclopentyl p-toluenesulfonate (1.80 kg, 7.48 mol), potassium carbonate (1.03 kg, 7.46 mol) and potassium iodide (12.3 g, 1.0 mol %), followed by the addition of solvent acetone (7,500 mL). The mixture was heated under reflux for 4 h. After completion of the reaction, the reaction mixture was recovered and 0.5N HCl (20 L) was added with vigorous stirring. The precipitating methyl N-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)carbamate as white solids (2.00 kg, 6.95 mol; yield=93.1%) was isolated by filtration and dried thoroughly. MP: 120.0°-123.0° C. 1H-NMR(CDCl3,TMS,ppm): δ1.40-2.10(8H,m), 3.77(3H,s), 4.77(1H,m), 6.82(1H,brs), 7.07(1H,d,JHF =10.5Hz), 7.83(1H,d,JHF =7.5Hz). IR (KBr disk, cm-1): 1714, 1535, 1500, 1415, 1255, 1190.

Workup

  1. customA 10-L three-necked flask equipped with a mechanical stirrer
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 4 h
  4. customAfter completion of the reaction
  5. customthe reaction mixture was recovered
  6. addition0.5N HCl (20 L) was added with vigorous stirring

Sources & evidence

ORD record
ord-5fed25bea4fc48b08d01a3a378b1f784
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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