Thionyl Chloride → HCID 86751386, compound

HRID 1489172Notes

Reaction equation

HRID 1489172 reaction equation
[CH2:1]([N:8]([CH2:16][C@@:17]1([CH2:34][F:35])[CH2:21][CH2:20][N:19]([C:22]2[C:30]([F:31])=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([F:32])[C:23]=2[F:33])[CH2:18]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:38])=O>ClCCCl.CN(C)C=O>[ClH:38].[CH2:1]([N:8]([CH2:16][C@@:17]1([CH2:34][F:35])[CH2:21][CH2:20][N:19]([C:22]2[C:30]([F:31])=[CH:29][C:25]([C:26]([Cl:38])=[O:27])=[C:24]([F:32])[C:23]=2[F:33])[CH2:18]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 54104441(S)-4-(3-(N,N-Dibenzylaminomethyl)-3-fluoromethylpyrrolidin-1-yl)-2,3,5-trifluorobenzoic acid

Product 1

HCID 86751386HCID 86751386, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

(S)-4-(3-(N,N-Dibenzylaminomethyl)-3-fluoromethylpyrrolidin-1-yl)-2,3,5-trifluorobenzoic acid (12.6 g) was dissolved in dry 1,2-dichloroethane (63 ml), and two drops of dry dimethylformamide were added. Thionyl chloride (2.3 ml) was added at room temperature and the mixture was refluxed for 2 hours. The reaction mixture was concentrated to give the object compound as pale-gray crystals, melting point 170°-173° C. (decomposition).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-65833f863dd74e34bd40c6de3ad46e39
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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