HCID 21483041, compound → HCID 21441048, compound

Participants

Reaction Steps

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).

Provenance & Evidence