Triphosgene → HCID 89783339, compound

HRID 1056435Notes

Reaction equation

HRID 1056435 reaction equation
[NH2:1][C:2]1[C:16]([Br:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[O:5].Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[Br:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:3]2[C:2]=1[NH:1][C:19](=[O:21])[N:6]([CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 89782334HCID 89782334, compound

Product 1

HCID 89783339HCID 89783339, compoundYield 330.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 2-amino-3-bromo-N-(2-(methylsulfonyl)ethyl)benzamide (480 mg, 1.494 mmol) and triphosgene (0.078 mL, 0.523 mmol, Fluka) in 1,4-dioxane (6 mL). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 45 min. The mixture was cooled to RT and the solvent was removed to give the crude product 600 mg. MS (ESI, pos. ion) m/z: 347 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. temperatureThe mixture was cooled to RT
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-1a3973aee6b749f4bdc5c407c5159337
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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