Triphosgene → HCID 178518248, compound

HRID 1774130Notes

Reaction equation

HRID 1774130 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]>O1CCOCC1>[Br:23][C:20]1[CH:19]=[C:15]2[C:14](=[CH:22][CH:21]=1)[N:13]=[C:2]([OH:4])[N:18]=[C:16]2[OH:17]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 50192712-Amino-5-bromobenzamide

Product 1

HCID 178518248HCID 178518248, compoundYield 164.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Triphosgene (173 g, 0.58 mmol) was added to a solution of 2-Amino-5-bromobenzamide (250 mg, 1.162 mmol) in 1,4-dioxane (12 mL). The reaction was heated at 100° C. for 1.5 hours, cooled to room temperature and quenched with water (1 ml). The solid was filtered and washed with EtOAc twice to provide crude product (230 mg), which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water (1 ml)
  3. filtrationThe solid was filtered
  4. washwashed with EtOAc twice

Sources & evidence

ORD record
ord-cd71582fd3ac45ff9d2e568953bcad49
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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