Dimethylsulphamoyl chloride → HCID 46181226, compound

HRID 2380973Notes

Reaction equation

HRID 2380973 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][N:30]([CH3:35])[S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH2:1]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18]2)=[O:16])=[CH:13][CH:14]=1)[S:31]([N:30]([CH3:35])[CH3:29])(=[O:33])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 67130440HCID 67130440, compound

Product 1

HCID 46181226HCID 46181226, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (4-benzylamino-phenyl)-(2-phenyl-morpholin-4-yl)-methanone (80 mg, 0.21 mmol) and N,N-dimethylsulfamoyl chloride (0.3 ml, 2 mmol) in pyridine (5 ml) was heated to 70° C. for 16 hours. The reaction was cooled then filtered and the filtrate diluted with dichloromethane (20 ml). The resulting solution was washed with hydrochloric acid 2N (20 ml), the organics collected and dried over magnesium sulfate. The solvent was removed in vacuo and the residue purified by preparative thin layer chromatography eluting with 50% ethylacetate/hexanes to afford the title compound as a colourless oil (35 mg, 35% yield). HPLC retention time 6.1 min. Mass spectrum (ES+) m/z 480 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthen filtered
  3. additionthe filtrate diluted with dichloromethane (20 ml)
  4. washThe resulting solution was washed with hydrochloric acid 2N (20 ml)
  5. customthe organics collected
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by preparative thin layer chromatography
  9. washeluting with 50% ethylacetate/hexanes

Sources & evidence

ORD record
ord-19ec916a5428487aae44985dc63cff11
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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