Hydrochloric Acid → HCID 178527799, compound

HRID 1404904Notes

Reaction equation

HRID 1404904 reaction equation
[C:1](=[S:3])=[S:2].C[O-].[Na+].Cl[C:8]1[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[CH:11][C:9]=1[NH2:10].Cl>CN(C=O)C.O>[Cl:16][C:12]1[C:13]([Cl:15])=[CH:14][C:8]2[S:2][C:1]([SH:3])=[N:10][C:9]=2[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 124872,4,5-TrichloroanilineHCID 10942334Sodium Methoxide

Product 1

HCID 178527799HCID 178527799, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
115 °C

Procedure

To a suspension of CS2 (0.64 mL, 10.6 mmol) and sodium methylate (0.55 g, 10.2 mmol) in DMF (10 mL) was added 2,4,5-trichloroaniline (7, 1.00 g, 5.09 mmol) in DMF (5 mL) under N2. The reaction mixture was heated at 110-120° C. for 16 h. After cooling, the reaction mixture was diluted with water (30 mL) and acidified with 1N HCl. The precipitate was collected by filtration, washed with water, and dried over P2O5 under vacuum to give yield compound 8 (1.06 g). This crude material was used in subsequent reactions without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialdried over P2O5 under vacuum
  5. customto give

Sources & evidence

ORD record
ord-8908b17fe6604e47bac950c009567f5d
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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