HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethyl Sulfoxide → 2,3,4,5,6,7-Hexahydro-1-(3-formyl-2-phenylpropanoyl)-1H-azepine

HRID 976099
Notes
Print preview

Reaction equation

HRID 976099 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:15]([N:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C>ClCCl>[CH:12]([CH2:13][CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:15]([N:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 199688572,3,4,5,6,7-Hexahydro-1-(4-hydroxy-2-phenylbutanoyl)-1H-azepine

Product 1

HCID 199688582,3,4,5,6,7-Hexahydro-1-(3-formyl-2-phenylpropanoyl)-1H-azepineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

Dimethylsulphoxide (3.97 g, 50.9 mmol) in dichloromethane (25 ml) was added to a solution of oxalyl chloride (3.09 g, 24.4 mmol) at -50° C. in dichloromethane (25 ml). The reaction mixture was kept at this temperature for 5 min, treated with a solution of the product of step (a) (5.54 g, 21.2 mmol) in dichloromethane (30 ml), and, after 1 h, treated with triethylamine (10.72 g, 0.106 mol). The cooling bath was removed and the reaction mixture allowed to warm to room temperature. Water (100 ml) was added and the separated aqueous phase washed with dichloromethane (50 ml). The combined organic phases were washed with brine (50 ml), water (50 ml), dried (Na2SO4) and concentrated in vacuo to afford the title compound as an oil (5.30 g, 96.4%).

Workup

  1. waitafter 1 h
  2. customThe cooling bath was removed
  3. additionWater (100 ml) was added
  4. washthe separated aqueous phase washed with dichloromethane (50 ml)
  5. washThe combined organic phases were washed with brine (50 ml), water (50 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8f27a525cbf468d994e7500d120b7e4
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05610295

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes