Diisopropylethylamine → HCID 67516544, compound

HRID 1754339Notes

Reaction equation

HRID 1754339 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12](=[O:14])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].Br[C:16]1C=C(C=CC=1C)C(=N)NO.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:16])[C:12](=[O:14])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 136121317HCID 136121317, compoundHCID 178425640HCID 178425640, compound

Product 1

HCID 67516544HCID 67516544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step-2: 3-(3-Bromo-4-methylphenyl)-1,2,4-oxadiazol-5(4H)-one: To a 0° C. cooled solution of 3-bromo-N-hydroxy-4-methylbenzimidamide (500 mg, 2.18 mmol, 1.0 eq) in DCM (10 mL) was added triphosgene (250 mg, 0.87 mmol, 0.4 eq) followed by diisopropylethylamine (0.76 mL, 4.46 mmol, 2 eq). The resulting mixture was stirred at room temperature for 3 h. The reaction was cooled back down to room temperature and quenched with water (5 mL) followed by dilution with DCM. The layers were separated and the organic layer was washed with brine (10 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under vacuum to afford 250 mg of the title product as white solid. 1HNMR (400 MHz, DMSO-d6) δ 13.10 (s, 1H, D2O exchangeable), 8.01 (d, J=1.5 Hz, 1H), 7.74 (dd, J=8.0, 1.5 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H) 2.42 (s, 3H); ESI-MS (m/z) 255, 257 [(MH)+, Br79,81]

Workup

  1. temperatureThe reaction was cooled back down to room temperature
  2. customquenched with water (5 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-e6fb452b7db64449aaeb615de65323b6
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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