Triethylamine → 7-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271082Notes

Reaction equation

HRID 2271082 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][CH:8]1[C:14]2[CH:15]=[C:16]([Cl:20])[CH:17]=[C:18]([CH3:19])[C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C>C1COCC1>[Cl:20][C:16]1[CH:17]=[C:18]([CH3:19])[C:13]2[O:12][CH2:11][CH2:10][CH2:9][CH:8]([NH:7][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 223917895-Amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

Product 1

HCID 223917937-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepineYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.86 g of ethanesulfonyl chloride was added dropwise with ice-cooling to a solution of 1.3 g of 5-amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine and 2.4 g of triethylamine in 30 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 and dried in vacuo. 1.6 g of 7-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine were obtained, m.p. 144-145° 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
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2395683f46e5417698c5c6252117a9e5
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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