Water → HCID 117600605, compound

HRID 1497720Notes

Reaction equation

HRID 1497720 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:10].C(N(CC)CC)C.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl.O>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:25](=[O:27])[O:10][CH:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 3305606HCID 3305606, compound

Product 1

HCID 117600605HCID 117600605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-Amino-5-bromo-phenyl)-phenyl-methanol (0.50 g, 1.798 mmol) is dissolved in anhydrous THF (25 mL). Triethylamine (0.55 g, 5.393 mmol) is added followed by triphosgene (0.16 g, 0.539 mmol). The mixture is stirred at room temperature overnight. Water (50 mL) is added and the reaction stirred for 15 minutes then extracted with ethylacetate (3×50 mL). The organic phases is washed with 1N HCl (2×50 mL) and a saturated solution of sodium hydrogencarbonate (50 mL). The organic phase is dried over sodium sulfate and concentrated in vacuo to provide the desired product as a white solid.

Workup

  1. stirringthe reaction stirred for 15 minutes
  2. extractionthen extracted with ethylacetate (3×50 mL)
  3. washThe organic phases is washed with 1N HCl (2×50 mL)
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bddd7773de94397ac2910383a1243ad
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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