Water → HCID 13477118, compound

HRID 370590Notes

Reaction equation

HRID 370590 reaction equation
Cl.[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19][NH2:20])=[CH:17][C:4]1=2.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[O:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:16]([CH2:18][CH2:19][NH:20][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:17][C:4]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13477123HCID 13477123, compound

Product 1

HCID 13477118HCID 13477118, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.5 g (0.014 m), of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethylamine of Example 6 and 1.4 g (0.014 m) of triethylamine in 50 ml of CH2Cl2, 1.6 g (0.014 m) of methanesulfonyl chloride was added dropwise maintaining the temperature between 15°-20° C. The mixture was stirred 45 minutes, then poured into water. The CH2Cl2 layer was separated, washed with water, dried (Na2SO4), filtered and evaporated to give a foamy solid. Recrystallization from approximately 40 ml of toluene gave 2.27 g (49%) of N-(2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl)methanesulfonamide, m.p. 104°-106° C.

Workup

  1. temperaturemaintaining the temperature between 15°-20° C
  2. customThe CH2Cl2 layer was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a foamy solid
  8. customRecrystallization from approximately 40 ml of toluene

Sources & evidence

ORD record
ord-4060d379c9a14f408e354972a8697ed6
Source dataset
uspto-grants-1985_07
Patent number
US04526891

Reaction notes

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