Methane → HCID 13043967, compound

HRID 1701898Notes

Reaction equation

HRID 1701898 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:15]([S:17]C)=S)[S:14][CH2:13][CH2:12][CH2:11][O:10]1.C>C(O)C>[CH3:1][NH:2][C:15]([C:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)[S:14][CH2:13][CH2:12][CH2:11][O:10]1)=[S:17]

Participants

5

Reactant 3

HCID 297MethaneHCID 6329MethylamineHCID 13043962HCID 13043962, compound

Product 1

HCID 13043967HCID 13043967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
2 °C

Procedure

A 33% (weight/volume) solution of methylamine in ethanol (6.5 cc) is added dropwise, in the course of 10 minutes and at a temperature between 34° C. and 37° C., to a solution of methyl 2-(pyrid-2-yl)-1,3-oxathiane-2-carbodithioate (17.5 g) in ethanol (60 cc). The reaction mixture is then stirred for 30 minutes at 2° C. The resulting crystals are filtered off, washed twice with petroleum ether (40 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. The product obtained (13.4 g) is dissolved in boiling ethanol (80 cc); decolourising charcoal (0.2 g) is added to the solution, which is filtered hot, and the filtrate is then cooled for 1 hour at a temperature of about 0° C. The resulting crystals are filtered off, washed twice with ethanol (20 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 50° C. N-Methyl-2-(pyrid-2-yl)-1,3-oxathiane-2-carbothioamide (12 g), melting at 157° C., is thus obtained.

Workup

  1. filtrationThe resulting crystals are filtered off
  2. washwashed twice with petroleum ether (40 cc in total)
  3. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C
  4. customThe product obtained (13.4 g)
  5. dissolutionis dissolved
  6. filtrationis filtered hot
  7. temperaturethe filtrate is then cooled for 1 hour at a temperature of about 0° C
  8. filtrationThe resulting crystals are filtered off
  9. washwashed twice with ethanol (20 cc in total)
  10. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 50° C

Sources & evidence

ORD record
ord-8457cd2db4c34576854cf7004e2a41c6
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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