Sodium Hydroxide → HCID 14210343, compound

HRID 652716Notes

Reaction equation

HRID 652716 reaction equation
O.S(=O)(=O)(O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:13](OC(=O)N)C.[C:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]=2[CH2:34][CH2:35][NH2:36])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O1CCCC1>[CH3:13][NH:36][CH2:35][CH2:34][C:26]1[NH:27][C:28]2[C:33]([C:25]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 21910475Sulfuric acid hydrate (1:1)HCID 70431093HCID 70431093, compound

Product 1

HCID 14210343HCID 14210343, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A cold solution of 8.6 ml sulphuric acid monohydrate in 85.6 ml tetrahydrofuran is added dropwise to a suspension of 12.1 g lithium aluminium hydride in 243 ml tetrahydrofuran at 0°. The mixture is stirred at 0° for 15 minutes and treated at 0° to 10° dropwise with 24.6 g 3-phenyl-1H-indol-2-ethanamine carbamic acid ethyl ester in 274 ml tetrahydrofuran. The mixture is heated under reflux for 45 minutes, then cooled to 0° and treated dropwise with 43 ml of a saturated sodium sulfate solution. 21 ml of 30% sodium hydroxide solution are further added and the mixture stirred for 1 hour. The mixture is filtered and the residue washed with ether. The filtrate is evaporated under reduced pressure and the residue cristallised from ether/pentane to give the heading compound, m.p. 148°-151°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturecooled to 0°
  4. stirringthe mixture stirred for 1 hour
  5. filtrationThe mixture is filtered
  6. washthe residue washed with ether
  7. customThe filtrate is evaporated under reduced pressure
  8. customto give the heading compound, m.p. 148°-151°

Sources & evidence

ORD record
ord-377d092a7fdb4a729413afbc5583a21d
Source dataset
uspto-grants-1987_06
Patent number
US04673674

Reaction notes

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