Triethylamine → HCID 21226931, compound

HRID 1391543Notes

Reaction equation

HRID 1391543 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:20](Cl)(Cl)=[S:21]>C1COCC1>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[NH:12][C:20]1=[S:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 21226931HCID 21226931, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N1-Methyl-4-nitro-benzene-1,2-diamine (1.0 g, 6.0 mmol) and triethylamine 2.5 ml (18 mmol) in THF (60 ml) was added thiophosgene (0.46 ml, 6.0 mmol) at 0° C. After 1 h, the reaction mixture was warmed up to rt and was stirred at room temperature for 3 h. After the starting material was consumed, the reaction was filtered. The collected solid was washed with EtOAc:Hexane=1:1 (10 ml×2) and water. The resulting yellow solid was dried to give the title compound (0.82 g, 66%). MS (ESI) m/z=209 [M+H].

Workup

  1. customAfter the starting material was consumed
  2. filtrationthe reaction was filtered
  3. washThe collected solid was washed with EtOAc
  4. customThe resulting yellow solid was dried

Sources & evidence

ORD record
ord-7193edbd770c4b5685cbf6ca0775aef9
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

Loading…