Water → HCID 18607004, compound

HRID 1906409Notes

Reaction equation

HRID 1906409 reaction equation
[OH:1][C@@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]=2[NH:4][C:3]1=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3.C(=O)([O-])[O-].[K+].[K+].[CH2:32]([N:34]([CH2:38][CH3:39])[CH2:35][CH2:36]Cl)[CH3:33].O>C(OCC)(=O)C>[CH2:32]([N:34]([CH2:38][CH3:39])[CH2:35][CH2:36][N:4]1[C:3](=[O:25])[C@H:2]([OH:1])[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:7][C:6]2[C:17]3[C:22]([CH:23]=[CH:24][C:5]1=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chloride2×HCID 13823434HCID 13823434, compound

Product 1

HCID 18607004HCID 18607004, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4.4 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one, 2.0 g of potassium carbonate and 1.8 g of 2-diethylaminoethyl chloride in 100 mL ethyl acetate was stirred and heated at reflux for 2 hours then an additional 0.5 g of 2-diethylaminoethyl chloride was added four times at 2 hour intervals. The mixture was heated at reflux for a total of 12 hours, then cooled to room temperature and to the mixture ethyl acetate and water were added. The organic phase was separated, washed with brine and dried (magnesium sulfate). Removal of the solvent gave the product which after crystallization from ether afforded 4.9 g (87%) (±)-cis-5-[2-(diethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one, mp 124°-125°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for a total of 12 hours
  5. additionwere added
  6. customThe organic phase was separated
  7. washwashed with brine
  8. dry with materialdried (magnesium sulfate)
  9. customRemoval of the solvent
  10. customgave the product which
  11. customafter crystallization from ether

Sources & evidence

ORD record
ord-29b0ff2b153b4afba9000f4dbabe9ff6
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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