3-Nitroaniline → (3-Nitrophenyl)thiourea

HRID 1490112Notes

Reaction equation

HRID 1490112 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[C:11](Cl)(Cl)=[S:12].C([N:17](CC)CC)C>O1CCCC1>[N+:8]([C:4]1[CH:3]=[C:2]([NH:1][C:11]([NH2:17])=[S:12])[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 10040Thiophosgene

Product 1

HCID 2754758(3-Nitrophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C. ) and stirred solution of 1-amino-3-nitrobenzene (10 g) in anhydrous tetrahydrofuran (500 ml), under nitrogen, was added thiophosgene (5.6 ml) dropwise. After 5 min triethylamine (29 ml) was added dropwise and the mixture stirred for a further 5 min at 0° C. then at room temperature for 10 min. The mixture was then re-cooled to 0° C. and ammonia gas bubbled through the mixture for 15 min. The resultant solid was removed by filtration and the filtrate evaporated in vacuo to afford a gum which was triturated with ethyl acetate to give the thiourea (7.3 g) as a solid. 1H NMR (250 MHz, D6 -DMSO)δ7.59 (1H, dd, J=8.2 and 8.2 Hz), 7.83 (1H, m), 7.92 (1H, m), 8.64 (1H, m), 10.09 (1H, brs). MS (CI, NH3) 197 (M+).

Workup

  1. waitat room temperature for 10 min
  2. temperatureThe mixture was then re-cooled to 0° C.
  3. customammonia gas bubbled through the mixture for 15 min
  4. customThe resultant solid was removed by filtration
  5. customthe filtrate evaporated in vacuo
  6. customto afford a gum which
  7. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-3798b429fddc490180dcf269817a5481
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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