Triethylamine → HCID 21467155, compound

HRID 1939191Notes

Reaction equation

HRID 1939191 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH:9](O)[C:8]2[S:14][CH:15]=[CH:16][C:7]1=2)=[O:5].C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2[S:14][CH:15]=[CH:16][C:7]1=2)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21467154HCID 21467154, compound

Product 1

HCID 21467155HCID 21467155, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.90 g of 4-(2-chloro-4-nitrobenzoyl)-8-hydroxy-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine in 5 ml of dichloromethane cooled to -10° C. is added under argon 533 μl of triethylamine and dropwise 296 μl of methanesulfonyl chloride. After one hour the cooling bath is removed and the mixture allowed to stand at room temperature overnight. The mixture is diluted with 10 ml of dichloromethane and 5 ml of water. The organic layer is separated, dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated under vacuum to give an oil which is crystallized by adding hexane. Filtration gives light yellow crystals (0.80 g).

Workup

  1. customAfter one hour the cooling bath is removed
  2. additionThe mixture is diluted with 10 ml of dichloromethane and 5 ml of water
  3. customThe organic layer is separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through a thin pad of hydrous magnesium silicate
  6. concentrationThe filtrate is concentrated under vacuum
  7. customto give an oil which
  8. customis crystallized
  9. additionby adding hexane
  10. filtrationFiltration

Sources & evidence

ORD record
ord-6ecae8b5712344d28d36b2a58f6651b9
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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