Thiophosgene → N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

HRID 1038959Notes

Reaction equation

HRID 1038959 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[C:12](Cl)([Cl:14])=[S:13]>ClCCl>[Cl-:14].[O:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH2:1][NH:11][CH:12]=[S:13])=[CH:3][C:4]=2[O:5][CH2:6]1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 75799Benzo-1,3-dioxole-5-methylamine

Product 1

HCID 86601006N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of piperonylamine (0.1 mL, 0.77 mmol) in dichloromethane (20 mL) was slowly added thiophosgene (0.06 mL, 0.83 mmol) under cooling with an ice bath. After the reaction mixture was stirred for four hours at room temperature, it was washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated and dried under vacuum; and the product was used immediately for the next reaction.

Workup

  1. temperatureunder cooling with an ice bath
  2. washit was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customdried under vacuum
  7. customand the product was used immediately for the next reaction

Sources & evidence

ORD record
ord-4dec44f39b5c4ecea65cb5ed984f11d5
Source dataset
uspto-grants-2013_10
Patent number
US08552018B2

Reaction notes

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