Thiophosgene → HCID 59860528, compound

HRID 1877331Notes

Reaction equation

HRID 1877331 reaction equation
[C:1](Cl)(Cl)=[S:2].[C:5]([O-])([O-])=O.[K+].[K+].[CH:11]1([NH2:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.[OH-].[K+]>ClCCl.O.CCOCC>[N:20]([CH:11]1[C:19]2[C:14](=[C:15]([CH3:5])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)=[C:1]=[S:2]

Participants

8

Reactant 4

HCID 10040ThiophosgeneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 123445(+-)-1-Aminoindan

Product 1

HCID 59860528HCID 59860528, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.36 ml (4.32 mmol) thiophosgene in 4 ml dichloromethane is cooled to 0° C. after which a cold (0° C.) solution of 0.5 g (3.60 mmol) K2CO3 in 4 ml water is added. The mixture is stirred for 10 min and 0.53 g (3.60 mmol) indan-1-ylamine is then added drop wise with vigorous stirring at 0° C. After an additional 10 min a cold solution of 0.40 g (7.20 mmol) KOH in 4 ml water is added in one portion with cooling. The organic layer and three extracts (Et2O) are combined, dried over MgSO4, filtered and concentrated to give 1-isothiocyanato-4-methyl-indane as an orange brown liquid. The product is used directly without further purification.

Workup

  1. additionis added
  2. stirringwith vigorous stirring at 0° C
  3. temperaturewith cooling
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22ad519de8e34d90bf2f2a920431146f
Source dataset
uspto-grants-2012_11
Patent number
US08309739B2

Reaction notes

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