Pyridine → HCID 71471186, compound

HRID 1628212Notes

Reaction equation

HRID 1628212 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].[NH2:11][NH:12][C:13]([NH2:15])=[S:14].N1C=CC=CC=1>O=S(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:11][NH:12][C:13]([NH2:15])=[S:14])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2369852-Chloroisonicotinic acidHCID 2723789Thiosemicarbazide

Product 1

HCID 71471186HCID 71471186, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

2-chloroisonicotinic acid 8.1.A (5000 mg, 31735 μmol) was refluxed in SOCl2 overnight under nitrogen. Another 4 mL of SOCl2 was added in the morning. After 2 hr., solution cleared up. The r×n was then concentrated and added to a thiosemicarbazide (2892 mg, 31735 μmol)/pyridine solution at 0° C. After 4 hr., LC/MS showed product MS along with many side peaks. The reaction was stopped and concentrated. Water and a small amount of EtOAc were added, precipitates were generated. Filtered and washed the precipitates with water 4 times. The solids were dried. LC/MS and the NMR of the precipitates showed to be the pure product. 4.05 g of the product 8.1.B (55%) was generated as a yellow powder.

Workup

  1. concentrationThe r×n was then concentrated
  2. waitAfter 4 hr
  3. concentrationconcentrated
  4. additionWater and a small amount of EtOAc were added
  5. customprecipitates
  6. filtrationFiltered
  7. washwashed the
  8. customprecipitates with water 4 times
  9. customThe solids were dried

Sources & evidence

ORD record
ord-9f0819c7779e4b60b09f6e236161592a
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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