Toluene → HCID 18473540, compound

HRID 429797Notes

Reaction equation

HRID 429797 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[S:11])=S.[OH-:12].[Na+].Cl[C:15](OCC)=[O:16].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=CC=1>O>[CH:20]1([O:12][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=2[O:16][CH3:15])[CH2:1][N:8]=[C:9]=[S:11])[CH2:25][CH2:24][CH2:23][CH2:26]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6348Carbon DisulfideHCID 7504BenzylamineHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide3×

Product 1

HCID 18473540HCID 18473540, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77.5 °C

Procedure

82.3 g (372 mmoles) of benzylamine were dissolved in 10 ml of toluene and added at 15-20° C. (with cooling) within 20 minutes to an emulsion of 22.5 ml (372 mmoles) of carbon disulfide and 14.88 g (372) mmoles) of NaOH in 52 ml of water. The reaction mixture was heated to 75-80° C. for 1 hour and cooled to 40° C. Within 15 minutes, 35.4 ml (372 mmoles) ethyl chloroformate were added at 40-45° C. The emulsion was brought to about pH 8 with 2N NaOH and heated to 55-60° C., gas formation ceased after about 10 hours keeping the pH at 8 with 2N NaOH (total about 8 ml). The organic layer was collected and the solvent evaporated: 96.3 g (98.3%) of benzyl isothiocyanate.

Workup

  1. additionadded at 15-20° C.
  2. temperaturecooled to 40° C
  3. temperatureheated to 55-60° C.
  4. waitgas formation ceased after about 10 hours
  5. customThe organic layer was collected
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-1152b9f184154094bb516b255fb5d823
Source dataset
uspto-grants-2001_11
Patent number
US06319928B1

Reaction notes

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