Methanesulfonyl chloride → HCID 88429211, compound

HRID 357255Notes

Reaction equation

HRID 357255 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:18]=[CH:19][S:20][C:3]1=2.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:21][S:22]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][C:4]3[CH:18]=[CH:19][S:20][C:3]=3[C:2](=[O:1])[C:8]=2[CH:9]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1351664-(4,10-Dihydro-10-oxothieno(3,2-c)(1)-benzoxepin-8-yl)butanol

Product 1

HCID 88429211HCID 88429211, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A chilled stirring solution of 9.5 g of 4-(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)butanol in 200 ml of sieve dried pyridine was treated dropwise with 3.80 g of methanesulfonyl chloride and the addition funnel was rinsed with a few ml of methylene chloride. The stirring solution was allowed to equilibrate to room temperature overnight with the bath in place. The resulting solution was poured into 750 ml of water and was allowed to stand for 15 min. The solids were collected by filtration, and dried in vacuo overnight at 42°0 C. Concentration of the mother liquor produced additional solids which were combined with the first crop and dried to give a total of 9.09 g of crude material. A 2.0 g portion of the product was recrystallized from hexane/ethyl acetate to give 1.3 g of 4-(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)butanol methanesulfonate, m.p. 97°-98° C.

Workup

  1. washthe addition funnel was rinsed with a few ml of methylene chloride
  2. additionThe resulting solution was poured into 750 ml of water
  3. waitto stand for 15 min
  4. filtrationThe solids were collected by filtration
  5. customdried in vacuo overnight at 42°0 C
  6. customConcentration of the mother liquor produced additional solids which
  7. customdried
  8. customto give a total of 9.09 g of crude material
  9. customA 2.0 g portion of the product was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-75d99f42bfe04605af956ed2bdd660b5
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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