HCID 21483041, compound → HCID 21441048, compound

HRID 1415627Notes

Reaction equation

HRID 1415627 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:10]=1[N+:19]([O-])=O)=[S:7])=[O:4]>CO.O>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:10]=1[NH2:19])=[S:7])=[O:4]

Participants

4

Reactant 1

HCID 21483041HCID 21483041, compound

Product 1

HCID 21441048HCID 21441048, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-Methoxycarbonyl-3-(4n-butyl-2-nitrophenyl)-thiourea (69.0 g; 0.22 mole) and ferrous chloride tetrahydrate (9.2 g) were finely powdered together and suspended in a mixture of methanol (350 ml) and water (70 ml). The vigorously stirred suspension was then heated to reflux and reduced iron powder (42.0 g; 0.78 mole) was added in portions during forty-five minutes. When the addition was complete, the reaction mixture was refluxed for a further thirty minutes and filtered. On cooling a crystalline solid separated from the filtrate. The dark brown filter cake was extracted with boiling methanol (3 × 200 ml) and the combined methanol extracts were evaporated to dryness to give a solid residue. This was combined with the solid obtained from the cold filtrate and the combined solids were crystallised from methanol to give 1-methoxycarbonyl-3-(2-amino-4-n-butylphenyl)thiourea (51.0 g), m.p. 157°-159° C. (with decomposition).

Workup

  1. temperatureThe vigorously stirred suspension was then heated
  2. temperatureto reflux
  3. additionWhen the addition
  4. temperaturethe reaction mixture was refluxed for a further thirty minutes
  5. filtrationfiltered
  6. temperatureOn cooling a crystalline solid
  7. customseparated from the filtrate
  8. extractionThe dark brown filter cake was extracted with boiling methanol (3 × 200 ml)
  9. customthe combined methanol extracts were evaporated to dryness
  10. customto give a solid residue
  11. customobtained from the cold filtrate
  12. customthe combined solids were crystallised from methanol

Sources & evidence

ORD record
ord-cee5cdde51e64d509646797755ac3d8f
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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