Water → 5-Methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271078Notes

Reaction equation

HRID 2271078 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C.O>C1COCC1>[CH3:1][S:2]([NH:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9][CH2:8]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 156196982,3,4,5-Tetrahydro-1-benzoxepin-5-amine

Product 1

HCID 223917905-Methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepineYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.54 g (13.4 mmol) of methanesulfonyl chloride were added dropwise with ice cooling to a solution of 2.0 g (12.2 mmol) of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine (Example 6b) and 3.7 g (36.6 mmol) of triethylamine in 40 ml of THF. The mixture was allowed to come to RT and was stirred overnight and treated with 50 ml of water, and the THF was distilled off in vacuo. The residue was diluted with a further 50 ml of water and stirred for 3 h, and the deposited product was filtered off with suction. After drying in vacuo, 2.2 g of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine were obtained, m.p. 105-106° C.

Workup

  1. customto come to RT
  2. distillationthe THF was distilled off in vacuo
  3. additionThe residue was diluted with a further 50 ml of water
  4. stirringstirred for 3 h
  5. filtrationthe deposited product was filtered off with suction
  6. customAfter drying in vacuo

Sources & evidence

ORD record
ord-c3b47cb6ef514ef2a80739637f0a4234
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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