Triethylamine → HCID 18319623, compound

HRID 1699388Notes

Reaction equation

HRID 1699388 reaction equation
[NH2:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:25][N:26]([CH3:31])[S:27](Cl)(=[O:29])=[O:28]>O1CCCC1>[CH3:25][N:26]([CH3:31])[S:27]([NH:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 18319514HCID 18319514, compound

Product 1

HCID 18319623HCID 18319623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 9-amino-2,3-dihydro-1-benzoxepin-4-carboxylate (1.0 g) and triethylamine (4.18 ml) in tetrahydrofuran (10 ml) was added dimethylsulfamoyl chloride (2.30 ml) at 5° C. The reaction mixture was stirred overnight at ambient temperature and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (4:1) to give ethyl 2,3-dihydro-9-dimethylsulfamoylamino-1-benzoxepin-4-carboxylate (0.89 g).

Workup

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4c93ed445ce1419f867f7a0a5687bed4
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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