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Methanesulfonyl chloride → 3-Tertiary-butoxycarbonyl-7-methanesulphonamido-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 329380
Notes
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Reaction equation

HRID 329380 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:24]=[CH:23][C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][C:9]=2[CH:8]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][S:2]([NH:6][C:7]1[CH:24]=[CH:23][C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15][C:9]=2[CH:8]=1)(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate

Product 1

HCID 187652003-Tertiary-butoxycarbonyl-7-methanesulphonamido-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.56 ml) was added dropwise to a solution of 7-amino-3-tertiary-butoxycarbonyl-1,2,4,5-tetrahydro-3H-3-benzazepine (1.9 g) in pyridine (40 ml) cooled to 0°. Stirring was continued at room temperature for 18 hours. The solvent was removed by evaporation to give an oil which was taken up in methylene chloride, washed three times with aqueous sodium bicarbonate and three times with brine, then dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 5%). The product-containing fractions were combined and evaporated in vacuo to give a semi-solid which was triturated with ether to give the title compound, yield 1.2 g, m.p. 153°-154°.

Workup

  1. temperaturecooled to 0°
  2. customThe solvent was removed by evaporation
  3. customto give an oil which
  4. washwashed three times with aqueous sodium bicarbonate and three times with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica eluting with methylene chloride
  8. additioncontaining methanol (0% up to 5%)
  9. customevaporated in vacuo
  10. customto give a semi-solid which
  11. customwas triturated with ether

Sources & evidence

ORD record
ord-be2e872a54714de394693a29380dc75a
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04891372

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes