Potassium Carbonate → HCID 15096195, compound

HRID 1587119Notes

Reaction equation

HRID 1587119 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][S:5][C:6]1[C:7]2[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[CH:17][C:8]=2[O:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([O:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:1][N:2]([CH2:3][CH2:4][S:5][C:6]1[C:7]2[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[CH:17][C:8]=2[O:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[CH:12]=1)[C:37]([O:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 14476081HCID 14476081, compound

Product 1

HCID 15096195HCID 15096195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 11.3 g of 11-[β-(dimethylamino)ethylthio]-2-(methylthio)dibenz[b,f]oxepin, free base of Example 21, and 10.0 g of potassium carbonate in 50 ml of methylene chloride is added dropwise a solution of 5.7 g of phenylchloroformate in 50 ml of methylene chloride. After total addition the reaction mixture is stirred at ambient temperature for 24 hours and then evaporated to dryness. The residue is triturated with ether and the ethereal solution is sequentially washed successively with a 10% sodium hydroxide solution and water, dried and filtered and the filtrate evaporated to dryness leaving a yellow oil. The oil is chromatographed through a silica gel column with a methylene chloride eluant to obtain the purified orange oil of 11-[β-(N-methyl-N-phenoxycarbonylamino)ethylthio]-2-(methylthio)-dibenz[b,f]oxepin.

Workup

  1. additionAfter total addition the reaction mixture
  2. customevaporated to dryness
  3. customThe residue is triturated with ether
  4. washthe ethereal solution is sequentially washed successively with a 10% sodium hydroxide solution and water
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness
  8. customleaving a yellow oil
  9. customThe oil is chromatographed through a silica gel column with a methylene chloride eluant

Sources & evidence

ORD record
ord-3fc5c2c9d7d94490bca356c8c00698d3
Source dataset
uspto-grants-1993_06
Patent number
US05216178

Reaction notes

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