N,N-Dimethylaniline → HCID 13015362, compound

HRID 1732473Notes

Reaction equation

HRID 1732473 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].C[N:17](C)C1C=CC=CC=1>>[NH2:17][C:9]1[C:8]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24533Sodium amideHCID 38136103-PHENYLTHIOPYRIDINE

Product 1

HCID 13015362HCID 13015362, compound

Procedure

A mixture of 59.1 g. (0.316 mole) of 3-phenylthiopyridine, 14.7 g. (0.318 mole) of sodium amide and 84 gms. of dimethyl aniline is heated at 150°-160° C. for 6 hours. After dilution with 100 ml. of water, the reaction mixture is extracted with chloroform. The combined extracts are washed with water and dried. Evaporation of the solvent in vacuo yields an oily residue. The residue is triturated with three 100 ml. portions of petroleum ether yielding 17 gm. of crude insoluble product. Proton magnetic resonance spectroscopy indicates the material is a 50/50 mixture of 2- and 6-amino derivatives. The isomers are separated on silica gel eluted with 10% ethylacetate 90% methylene chloride affording pure 2-amino 3-(phenylthio) pyridine, m.p. 108°-109° C.

Workup

  1. additionA mixture of 59.1 g
  2. extractionof water, the reaction mixture is extracted with chloroform
  3. washThe combined extracts are washed with water
  4. customdried
  5. customEvaporation of the solvent in vacuo
  6. customyields an oily residue
  7. customThe residue is triturated with three 100 ml
  8. additiona 50/50 mixture of 2- and 6-amino derivatives
  9. customThe isomers are separated on silica gel
  10. washeluted with 10% ethylacetate 90% methylene chloride affording pure 2-amino 3-(phenylthio) pyridine, m.p. 108°-109° C.

Sources & evidence

ORD record
ord-3f2d856b4ab1496194205abc642730a5
Source dataset
uspto-grants-1980_12
Patent number
US04237300

Reaction notes

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