Methanesulfonyl chloride → HCID 19872045, compound

HRID 329365Notes

Reaction equation

HRID 329365 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:26])[CH:20]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:2]([CH3:1])(=[O:4])=[O:3])=[C:21]([CH3:26])[CH:20]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19872052HCID 19872052, compound

Product 1

HCID 19872045HCID 19872045, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.18 ml) was added dropwise to a solution of 7-amino-3-[2-(4-amino-3-methylphenoxy)ethyl]-1,2,4,5-tetrahydro-3H-3-benzazepine (0.36 g) in pyridine (30 ml) cooled to 0°, and the mixture was then stirred at room temperature for 72 hours. The solvent was evaporated in vacuo and the residue was taken up in methylene chloride and washed three times with saturated aqueous sodium bicarbonate and three times with brine. The organic layer was dried (Na2SO4), filtered and evaporated in vacuo to give an oil which was triturated with methylene chloride to give a solid. Recrystallisation of the solid from ethanol/ethyl acetate gave the title compound, yield 0.28 g, m.p. 173°-174°.

Workup

  1. temperaturecooled to 0°
  2. customThe solvent was evaporated in vacuo
  3. washwashed three times with saturated aqueous sodium bicarbonate and three times with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give an oil which
  8. customwas triturated with methylene chloride
  9. customto give a solid
  10. customRecrystallisation of the solid from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-09470cea555b4addb556e703b08b9d07
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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