Sodium hydrosulfide → HCID 178508135, compound

HRID 1396594Notes

Reaction equation

HRID 1396594 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

A mixture of 4,6-dichloropyrimidine-5-amine (E-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 resulting mixture is allowed to cool to RT and then concentrated in vacuo. The residue is poured into aqueous NaOH solution (200 mL, 1 M) and then neutralized with acetic acid to adjust the pH value 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 (E-3).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue is poured into aqueous NaOH solution (200 mL, 1 M)
  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-91af63f5177e4361ae27d602da763c33
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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