Triethylamine → HCID 90019801, compound

HRID 2200134Notes

Reaction equation

HRID 2200134 reaction equation
C(N(CC)CC)C.Cl[C:9](Cl)([O:11]C(=O)OC(Cl)(Cl)Cl)Cl.[Br:20][C:21]1[CH:22]=[C:23]([NH:31][CH2:32][CH:33]([OH:35])[CH3:34])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1>ClCCl>[Br:20][C:21]1[CH:22]=[C:23]([N:31]2[CH2:32][CH:33]([CH3:34])[O:35][C:9]2=[O:11])[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 65490426HCID 65490426, compound

Product 1

HCID 90019801HCID 90019801, compoundYield 195.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (339 mg, 3.35 mmol) and triphosgene (250 mg, 0.838 mmol) to the solution of 1-(3-bromo-5-(trifluoromethyl)phenylamino)propan-2-ol (500 mg, 1.68 mmol) in dichloromethane (8 mL), stir the resulting mixture overnight at ambient temperature. Partition the reaction mixture between dichloromethane and water, separate the organic layer, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to give the crude product. Purify with flash chromatography (silica gel, PE:EtOAc=1:1) to afford the product (530 mg, 97%). MS: (M+1): 324.0.

Workup

  1. customPartition the reaction mixture between dichloromethane and water
  2. customseparate the organic layer
  3. dry with materialdry over anhydrous sodium sulfate
  4. concentrationconcentrate under reduced pressure
  5. customto give the crude product
  6. customPurify with flash chromatography (silica gel, PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-6782289c0f094fcc9e32b40ba22d6244
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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