Triethylamine → HCID 21226931, compound

HRID 1391539Notes

Reaction equation

HRID 1391539 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][NH:6][C:7]1[C:8]([NH2:16])=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1.CCN(CC)CC>C1COCC1>[CH3:5][N:6]1[C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[NH:16][C:1]1=[S:2]

Participants

5

Reactant 3

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

Product 1

HCID 21226931HCID 21226931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of thiophosgene (2.3 ml, 30 mmol) in THF (300 ml) was added dropwise to a solution containing N1-Methyl-4-nitro-benzene-1,2-diamine (5.01 g, 30 mmol) and Et3N (9.2 ml, 66 mmol) in THF (300 ml) at 0° C. over 90 min. After stirring at 0° C. for another 1 hr, the mixture was allowed to warm to room temperature. The mixture was then concentrated to about 100 ml, water (200 ml) was added, the mix was stirred for 20 min, the product was collected by filtration and washed with small amount of cold CH2Cl2, after drying left 5.16 g as a mustard yellow solid: LC/MS (m/e) at 210.0 [M+H]+, Rt at 1.49 min.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe mixture was then concentrated to about 100 ml, water (200 ml)
  3. additionwas added
  4. stirringthe mix was stirred for 20 min
  5. filtrationthe product was collected by filtration
  6. washwashed with small amount of cold CH2Cl2
  7. customafter drying
  8. waitleft 5.16 g as a mustard yellow solid
  9. customat 1.49 min.

Sources & evidence

ORD record
ord-e2761aaccd444fc2a5cfc77be66ec0ae
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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