Triphosgene → HCID 12724207, compound

HRID 877017Notes

Reaction equation

HRID 877017 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.O>[CH3:10][C:4]1[S:3][C:2]2[NH:1][C:12](=[O:14])[NH:9][C:7](=[O:8])[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 136257322-Amino-5-methylthiophene-3-carboxamide

Product 1

HCID 12724207HCID 12724207, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Step 2 intermediate (16.5 g, 94.82 mmol) in dry THF (316 ml) was added triphosgene (14.07 g, 47.41 mmol) and the mixture was refluxed for overnight under nitrogen atmosphere. The mixture was cooled to room temperature and diluted with water (200 ml) under stirring. The solid precipitated out was collected by filtration and dried to give 13.8 g of the desired product; 1H NMR (300 MHz, DMSO-d6) δ 2.36 (s, 3H), 6.82 (s, 1H), 11.07 (br. s, 1H), 11.79 (br. s, 1H).

Workup

  1. temperaturethe mixture was refluxed for overnight under nitrogen atmosphere
  2. customThe solid precipitated out
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-29ce839f16be474a976c95bc9faa2150
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

Loading…