Methyl chloroformate → Methyl (3-chloro-2-methylphenyl)carbamate

HRID 1048615Notes

Reaction equation

HRID 1048615 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].O1CCCC1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=1[CH3:19]>O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:2]([O:4][CH3:5])=[O:3])[C:13]=1[CH3:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 68943-Chloro-2-methylanilineHCID 8028Tetrahydrofuran

Product 1

HCID 5045840Methyl (3-chloro-2-methylphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Under cooling, to a mixture of methyl chloroformate 30 mL and tetrahydrofuran 50 mL was added dropwise 1-chloro-2-methyl-3-aminobenzene 5.00 g and the mixtures were stirred at 25° C. for a half hour. To the reaction mixtures was added water and the resulting mixtures were extracted with ethyl acetate. The organic layers were washed with aqueous saturated sodium bicarbonate solution and were dried over anhydrous sodium sulfate. The mixtures were concentrated under reduced pressure to give 1-chloro-2-methyl-3-methoxycarbonylaminobenzene 5.80 g.

Workup

  1. customTo the reaction mixtures
  2. extractionthe resulting mixtures were extracted with ethyl acetate
  3. washThe organic layers were washed with aqueous saturated sodium bicarbonate solution
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. concentrationThe mixtures were concentrated under reduced pressure

Sources & evidence

ORD record
ord-dcc38955e6714627b69d85307b2d3c3a
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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