Triethylamine → 5-Ethylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271076Notes

Reaction equation

HRID 2271076 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C>C1COCC1>[CH2:1]([S:3]([NH:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 156196982,3,4,5-Tetrahydro-1-benzoxepin-5-amine

Product 1

HCID 223918085-Ethylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepineYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.86 g (6.7 mmol) of ethanesulfonyl chloride was added dropwise with ice cooling to a solution of 1.0 g (6.1 mmol) of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine and 2.5 g (24 mmol) of triethylamine in 20 ml of THF. The mixture was allowed to come to room temperature and was stirred overnight, and the solvent was distilled off in vacuo. After stirring the residue with water, the deposited product was filtered off with suction. 1.1 g of 5-ethylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine were obtained, m.p. 109-111° C.

Workup

  1. customto come to room temperature
  2. distillationthe solvent was distilled off in vacuo
  3. stirringAfter stirring the residue with water
  4. filtrationthe deposited product was filtered off with suction

Sources & evidence

ORD record
ord-65e51f8995e14c3191e70cd612fa0e0d
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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