Triphosgene → HCID 85903656, compound

HRID 2114615Notes

Reaction equation

HRID 2114615 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]([F:18])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:19][C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:9][C:10]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]([F:18])[CH:11]=2)[C:20]([Cl:19])=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 551475353-Fluoro-N-[(3,4,5-trifluorophenyl)methyl]aniline

Product 1

HCID 85903656HCID 85903656, compoundYield 124.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.4 g (13.30 mmol) of 3-fluorophenyl-(3,4,5-trifluorobenzyl)amine (Intermediate I-8) in 25 ml of methylene chloride, cooled at −10° C., was added slowly with stirring a solution of 2.0 g (6.70 mmol) of triphosgene in 15 ml of methylene chloride. The reaction was allowed to warm to room temperature and stirred for 17 hours at this temperature. After this time the solid formed during the process was filtered and the filtrate was concentrated in vacuo. The obtained residue was treated with n-hexane at −25° C. The soluble part was separated and filtrated. The filtrate was concentrated in vacuo to dryness to give 2.65 g (62.8%) of the tide product as an oil. The structure was confirmed by 1H-NMR.

Workup

  1. additionwas added slowly
  2. customAfter this time the solid formed during the process
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe obtained residue was treated with n-hexane at −25° C
  6. customThe soluble part was separated
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-d9738d0a71fa4981bb188ea83efbfb4e
Source dataset
uspto-grants-2008_10
Patent number
US07435742B2

Reaction notes

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