35198-73-3 → HCID 21412481, compound

HRID 2071799Notes

Reaction equation

HRID 2071799 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6](=[S:25])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[NH:17][C:18]([NH:20][C:21]([O:23][CH3:24])=[O:22])=[S:19])=[O:4]>CO.O>[CH3:24][O:23][C:21]([NH:20][C:18](=[S:19])[NH:17][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:8]=1[NH:7][C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])=[S:25])[NH2:14])=[O:22]

Participants

4

Reactant 1

HCID 348172435198-73-3

Product 1

HCID 21412481HCID 21412481, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,2-Bis-(3-methoxycarbonyl-2-thioureido)-4-nitrobenzene (9.7 g; 0.025 mole) and ferrous chloride tetrahydrate (1.13 g) were finely powdered together and suspended in a mixture of methanol (110 ml) and water (10 ml). The vigorously stirred suspension was then heated to reflux and reduced iron powder (6.53 g) was added in portions during five minutes. When the addition was complete, the reaction mixture was refluxed for a further forty five minutes and filtered. The dark brown filter cake was extracted with boiling methanol (2 × 120 ml), and the hot methanol solutions were combined with the hot aqueous methanol filtrate and evaporated to 200 ml. The solution was cooled to room temperature and the solid which separated was filtered off to give 3,4-bis-(3-methoxycarbonyl-2-thioureido)aniline (4.70 g), m.p. 186-187° C. (with decomposition), in the form of off-white crystals.

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 forty five minutes
  5. filtrationfiltered
  6. extractionThe dark brown filter cake was extracted with boiling methanol (2 × 120 ml)
  7. customevaporated to 200 ml
  8. customthe solid which separated
  9. filtrationwas filtered off

Sources & evidence

ORD record
ord-920ff631b0a841038e5d43a6f2dc178e
Source dataset
uspto-grants-1977_09
Patent number
US04048326

Reaction notes

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