Sodium hydrosulfide → HCID 178508135, compound

HRID 2173462Notes

Reaction equation

HRID 2173462 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[SH-:10].[Na+]>CO>[NH2:8][C:7]1[C:6]([SH:10])=[N:5][CH:4]=[N:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 178508135HCID 178508135, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4,6-dichloropyrimidine-5-amine (A-2) (16.0 g, 98.2 mmol) and sodium hydrosulphide (7.15 g, 128 mmol) in MeOH (320 mL) is stirred at reflux for 3 h. The reaction is complete based on TLC analysis. The reaction mixture is allowed to cool to RT and then concentrated in vacuo. The residue is poured into aqueous NaOH solution (1M, 200 mL) and then neutralized with acetic acid to adjust the pH to 5-6. The resulting mixture is stirred at RT for 30 min. The solid is collected by filtration, rinsed with water (2×50 mL) and dried in vacuo to afford the product, 5-amino-6-chloropyrimidine-4-thiol (A-3).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue is poured into aqueous NaOH solution (1M, 200 mL)
  4. stirringThe resulting mixture is stirred at RT for 30 min
  5. filtrationThe solid is collected by filtration
  6. washrinsed with water (2×50 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6052ff74e1584b5ba679e0d7d79f8158
Source dataset
uspto-grants-2015_06
Patent number
US09056877B2

Reaction notes

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