Methane → HCID 13043964, compound

HRID 1701888Notes

Reaction equation

HRID 1701888 reaction equation
[CH3:1][NH2:2].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1([C:18]([S:20]C)=S)[CH2:17][CH2:16][CH2:15][S:14]1.C>C(O)C>[CH3:1][NH:2][C:18]([C:13]1([C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:3]=2)[CH2:17][CH2:16][CH2:15][S:14]1)=[S:20]

Participants

5

Reactant 3

HCID 297MethaneHCID 6329MethylamineHCID 13043959HCID 13043959, compound

Product 1

HCID 13043964HCID 13043964, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
20 °C

Procedure

A 33% (weight/volume) solution of methylamine in ethanol (13.5 cc) is added dropwise and in the course of 10 minutes to a suspension of methyl 2-(quinol-2-yl)-tetrahydrothiophen-2-carbodithioate (20 g) in ethanol (42 cc), kept at a temperature of about 20° C. The reaction mixture is then stirred for 15 hours at a temperature of about 20° C. The resulting crystals are filtered off, washed twice with ethanol (24 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. A crystalline crude product (12.1 g) is thus obtained. This product is redissolved in boiling ethanol (75 cc); decolourising charcoal (0.6 g) is added to the solution, which is filtered hot, and the filtrate is then cooled for 3 hours at a temperature of about 5° C. The resulting crystals are filtered off, washed twice with ethanol (24 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C. N-Methyl-2-(quinol-2-yl)-tetrahydrothiophen-2-carbothioamide (11 g), melting at 124° C., is thus obtained.

Workup

  1. customkept at a temperature of about 20° C
  2. filtrationThe resulting crystals are filtered off
  3. washwashed twice with ethanol (24 cc in total)
  4. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C
  5. customA crystalline crude product (12.1 g) is thus obtained
  6. dissolutionThis product is redissolved
  7. filtrationis filtered hot
  8. temperaturethe filtrate is then cooled for 3 hours at a temperature of about 5° C
  9. filtrationThe resulting crystals are filtered off
  10. washwashed twice with ethanol (24 cc in total)
  11. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-0058fdd35cc340ec964ea354379485ee
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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