Sodium Hydroxide → HCID 22115238, compound

HRID 1276213Notes

Reaction equation

HRID 1276213 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)[CH2:8][CH2:9]O)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]1[S:27][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 15790727HCID 15790727, compound

Product 1

HCID 22115238HCID 22115238, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 g (14.4 mmol) of N-(2,6-difluorobenzoyl)-3-amino-3-(4-tert-butylphenyl)-1-propanol, 3.2 g (14.4 mmol) of phosphorus pentasulfide and 30 ml of toluene is heated under reflux for 6 hours. The mixture is allowed to cool, 10 ml of 20% strength aqueous sodium hydroxide solution are added and the mixture is heated under reflux for 30 minutes. After customary working up, the crude product is purified by column chromatography on silica gel (mobile phase n-hexane/ethyl acetate 8/2). 2.7 g (54.3%) of 2-(2,6-difluorophenyl)-4-(4-tert-butylphenyl)-5,6-dihydro-(4H)1,3-thiazine of melting point 91.0-91.5° C. are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 30 minutes
  6. customthe crude product is purified by column chromatography on silica gel (mobile phase n-hexane/ethyl acetate 8/2)

Sources & evidence

ORD record
ord-5cd8ecc3cb534724a33ded5325008efe
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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