Dimethylamine → HCID 13208960, compound

HRID 1583912Notes

Reaction equation

HRID 1583912 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2O)=[CH:7][C:6]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17].P(Cl)(Cl)(Cl)(Cl)[Cl:26].[CH3:31][NH:32][CH3:33]>ClCCl.C(OCC)C.ClCCl>[ClH:26].[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[N:32]([CH3:33])[CH3:31])=[CH:7][C:6]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 24819Phosphorus pentachlorideHCID 13084202N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamide

Product 1

HCID 13208960HCID 13208960, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

2.84 g of N-[6-(2,4-difluorophenoxy)-1-hydroxy-5-indanyl]methanesulfonamide and 1.83 g of phosphorus pentachloride are stirred in 50 ml of dichloromethane-diethyl ether (1:1) for 45 minutes at 0° C. At 0° C., a solution of 7 g of dimethylamine in 25 ml of dichloromethane is added to the reaction mixture. After 2 hours at 20° C. and 20 minutes of boiling, the mixture is concentrated and the residue is recrystallized from aqueous hydrochloric acid, yielding 2.41 g of N-[6-(2,4-difluorophenoxy)-1-dimethylamino-5-indanyl]methanesulfonamide, hydrochloride, mp 195° C.

Workup

  1. custom20 minutes
  2. concentrationthe mixture is concentrated
  3. customthe residue is recrystallized from aqueous hydrochloric acid

Sources & evidence

ORD record
ord-161c7797c8854fe1a6d91047e0d56461
Source dataset
uspto-grants-1985_11
Patent number
US04555406

Reaction notes

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