Sodium Hydroxide → HCID 19766136, compound

HRID 1591045Notes

Reaction equation

HRID 1591045 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[S:25][CH2:24][CH2:23][NH:22][C:21](=O)[CH2:20]2)=[CH:15][CH:14]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1.O>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[S:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 12596983HCID 12596983, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19766136HCID 19766136, compoundYield 57.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (190 mL of a 1M ethereal solution) is cooled to 0° C. and treated with aluminum chloride (8.44 g, 63.2 mmol) in 15 mL of diethyl ether. The resulting clear solution is stirred at 0° C. for 20 minutes and then a slurry of tetrahydro-7-(4-methoxyphenyl)-1,4-thiazepin 5-one (15.0 g, 63.2 mmol) in 150 mL of tetrahydrofuran is added. The reaction is then allowed to warm to room temperature for 12 hours and is treated with 14.4 mL of water, 7.2 mL of a 10% aqueous sodium hydroxide solution and 36 mL of water. The mixture is stirred for 3 hours and filtered. The filtrate is concentrated to obtain 8.14 g of a clear oil. The oil is converted to the hydrochloride salt; mp 209°-212° C.

Workup

  1. temperatureto warm to room temperature for 12 hours
  2. stirringThe mixture is stirred for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-db4857bbe48a4b90937b5558e89d7216
Source dataset
uspto-grants-1993_04
Patent number
US05206233

Reaction notes

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