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

HRID 2056332Notes

Reaction equation

HRID 2056332 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-53ea23cae29b491a897930b36780d4e8
Source dataset
uspto-grants-2008_02
Patent number
US07335662B2

Reaction notes

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