Triphosgene → HCID 178518411, compound

HRID 1093295Notes

Reaction equation

HRID 1093295 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[N:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([OH:8])=[N:9][C:11]=1[OH:13]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 5189933-Aminothiophene-2-carboxamide

Product 1

HCID 178518411HCID 178518411, compoundYield 146.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

500 mg (3.5 mmol) 3-amino-thiophene-2-carboxamide is dissolved in 30 mL dioxane. 520 mg (1.75 mmol, 0.5 eq) triphosgene is added and the mixture is heated at 80 C for 1 h. The mixture is concentrated and triturated from hot methanol. The resulting solids are collected. The filtrate is concentrated and triturated again from hot methanol. The 2 crops of solids are combined to give 432 mg of the title compound (2.57 mmol, 73%).

Workup

  1. temperaturethe mixture is heated at 80 C for 1 h
  2. concentrationThe mixture is concentrated
  3. customtriturated from hot methanol
  4. customThe resulting solids are collected
  5. concentrationThe filtrate is concentrated
  6. customtriturated again from hot methanol

Sources & evidence

ORD record
ord-ed85e046d0e6416abb0d6dbf1d757277
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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