Water → methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate

HRID 2414263Notes

Reaction equation

HRID 2414263 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:15])=[C:7]([CH:14]=1)[CH2:8][NH:9][C:10](=[O:13])[O:11][CH3:12].[C-:16]#[N:17].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[Cl:15][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][C:16]#[N:17])=[CH:14][C:7]=1[CH2:8][NH:9][C:10](=[O:13])[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22645123methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate

Product 1

HCID 12151315methyl N-(2-chloro-5-cyanomethylbenzyl)carbamateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.3 g of the methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate obtained in Reference Example 3 was dissolved in 20 ml of N,N-dimethylformamide, and 0.43 g of sodium cyanide was added thereto at 0° C. Stirring was carried out at 0° C. for 1 hour, and stirring was carried out further for 4 hours at room temperature, then water was added to the reaction mixture, extraction with ethyl acetate was carried out, and the organic solvent was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with hexane to obtain 1.3 g of methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate as white crystals.

Workup

  1. customat 0° C
  2. stirringstirring
  3. waitwas carried out further for 4 hours at room temperature
  4. dry with materialthe organic solvent was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained crude crystals
  7. washwere washed with hexane

Sources & evidence

ORD record
ord-a9ec752451f644f3b4de74b0f20d79a4
Source dataset
uspto-grants-2004_11
Patent number
US06812229B1

Reaction notes

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