Thiophosgene → HCID 59646493, compound

HRID 1898294Notes

Reaction equation

HRID 1898294 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH2:8].C(N(C(C)C)C(C)C)C.[C:19](Cl)(Cl)=[S:20]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[N:8]=[C:19]=[S:20]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 81531DiisopropylethylamineHCID 898884-Amino-3,5-dichloropyridine

Product 1

HCID 59646493HCID 59646493, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,5-dichloropyridin-4-amine (4.0 g, 24.53 mmol) in DCM (20 mL), was added N-ethyl di-isopropyl amine (6.3 g, 48.83 mmol). The reaction mixture was stirred at RT for 30 minutes. The reaction mixture was cooled at 0° C. and thiophosgene (2.76 g, 24.00 mmol) was added drop wise. The reaction mixture was stirred at 0° C. to RT for 3-4 h. The reaction mixture was diluted with DCM and the obtained crude was purified by column chromatography to afford 1.0 g of the desired product. 1HNMR (DMSO-d6): δ 8.77 (s, 2H); MS [M+H]+: 205.20.

Workup

  1. temperatureThe reaction mixture was cooled at 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. to RT for 3-4 h
  3. customthe obtained crude
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6e05c3a4ed6a46dabf279daa4b73223f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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