Water → HCID 9841326, compound

HRID 345959Notes

Reaction equation

HRID 345959 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].O.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[NH2:7][C:1]1[C:2]2[C:3]3[CH:4]=[CH:5][CH:20]=[CH:21][C:22]=3[C:23](=[O:19])[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[S:9][C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 5

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 60984Methyl bromoacetate

Product 1

HCID 9841326HCID 9841326, compound

Procedure

To a solution of 17.5 g of methyl 2-cyanomethyl benzoate and 16.2 g of phenyl isothiocyanate in 300 ml of tetrahydrofuran was added 4.8 g of a 60% sodium hydride for 20 minutes under an ice-cooling in a stream of nitrogen, and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 18.4 g of methyl bromoacetate for 15 minutes, and then the mixture was stirred for 1 hour. To the reaction mixture was added 4.8 g of a 60% sodium hydride, and the mixture was stirred for 14 hours. The reaction mixture was poured into 3 l of water, and the precipitates were collected by a filtration. The precipitates were successively washed with water and acetone, and air-dried, and dried over phosphorus pentaoxide to obtain 25.3 g of the desired product as brown crystals.

Workup

  1. temperaturecooling in a stream of nitrogen
  2. stirringthe mixture was stirred for 1 hour
  3. stirringthe mixture was stirred for 14 hours
  4. filtrationthe precipitates were collected by a filtration
  5. washThe precipitates were successively washed with water and acetone
  6. customair-dried
  7. dry with materialdried over phosphorus pentaoxide

Sources & evidence

ORD record
ord-2bcba7d85919450ba0198084261e97a5
Source dataset
uspto-grants-1991_10
Patent number
US05059692

Reaction notes

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