Water → HCID 178425677, compound

HRID 2308614Notes

Reaction equation

HRID 2308614 reaction equation
O.[SH-:2].[Na+].Br[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[O:12])[N:6]=1.O>C(O)CO>[C:16]1([CH3:19])[CH:17]=[CH:18][C:13]([C:11]([C:7]2[N:6]=[C:5]([SH:2])[CH:10]=[CH:9][CH:8]=2)=[O:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13191750(6-Bromo-2-pyridinyl)(4-methylphenyl)methanoneHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 178425677HCID 178425677, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of sodium hydrosulphide hydrate (22.0 g) in ethylene glycol (100 ml) at 100° C. was added 2-bromo-6-(4-toluoyl)pyridine (27.6 g) in portions. The mixture was then heated at 110° C. for 3 hours, allowed to cool and then poured into water (600 ml). The yellow precipitate of the by-product 6-(4-methylbenzyl)pyridine-2-thiol was filtered off and the filtrate was acidified by the addition of glacial acetic acid (10 ml). The resultant orange solid was then filtered off and well washed with water and dried. This crude solid (19.4 g) was crystallised from a mixture of benzene (500 ml) and methanol (175 ml) to give 6-(4-toluoyl)pyridine-2-thiol (10.0 g) as orange needles. M.p. 179°-181°.

Workup

  1. temperatureto cool
  2. filtrationThe yellow precipitate of the by-product 6-(4-methylbenzyl)pyridine-2-thiol was filtered off
  3. additionthe filtrate was acidified by the addition of glacial acetic acid (10 ml)
  4. filtrationThe resultant orange solid was then filtered off
  5. washwell washed with water
  6. customdried
  7. customThis crude solid (19.4 g) was crystallised from a mixture of benzene (500 ml) and methanol (175 ml)

Sources & evidence

ORD record
ord-5e70b8f68f3e43d6b9935fc37ed3bacb
Source dataset
uspto-grants-1987_09
Patent number
US04690933

Reaction notes

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