Methoxycarbonyl isothiocyanate → 4-Carbamoylthio-1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene

HRID 616128Notes

Reaction equation

HRID 616128 reaction equation
NC1C=CC(SC(=O)N)=CC=1[N+]([O-])=O.[C:15]([S:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]([O:31][CH3:32])=[O:30])=[S:27])=[C:21]([N+:33]([O-])=O)[CH:20]=1)(=[O:17])[NH2:16].NC1C=CC(SC(=O)N)=CC=1N.[CH3:48][O:49][C:50]([N:52]=[C:53]=[S:54])=[O:51]>[Fe].CC(C)=O>[C:15]([S:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]([O:31][CH3:32])=[O:30])=[S:27])=[C:21]([NH:33][C:53]([NH:52][C:50]([O:49][CH3:48])=[O:51])=[S:54])[CH:20]=1)(=[O:17])[NH2:16]

Participants

7

Reactant 4

HCID 552246Methoxycarbonyl isothiocyanateHCID 189497711-Amino-4-carbamoylthio-2-nitrobenzeneHCID 203711621,2-Diamino-4-carbamoylthiobenzeneHCID 203711724-Carbamoylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

Product 1

HCID 203712244-Carbamoylthio-1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 23925IronSolvent

Procedure

In a similar manner, substituting 1-amino-4-carbamoylthio-2-nitrobenzene for the 4-carbamoylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene in the iron reduction step, 1,2-diamino-4-carbamoylthiobenzene is prepared. 0.5 G. of this latter compound in 30 ml. acetone is treated overnight with 2 g. methoxy carbonyl isothiocyanate at room temperature. The solution is concentrated and the residue triturated with ether. Recrystallization yields 4-carbamoylthio-1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene.

Workup

  1. customis prepared
  2. customat room temperature
  3. concentrationThe solution is concentrated
  4. customthe residue triturated with ether
  5. customRecrystallization

Sources & evidence

ORD record
ord-acd96665fa7d4ca0b5f857d9849ea754
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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