Hydrochloric Acid → HCID 14255702, compound

HRID 1638252Notes

Reaction equation

HRID 1638252 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:14]2[S:15][CH:16]([CH3:18])[CH2:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:24][O:25][CH2:26]Br.Cl>O1CCCC1.CCCCCC>[C:1]([NH:5][S:6]([C:9]1[C:14]2[S:15][CH:16]([CH3:18])[CH2:17][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:24][O:25][CH3:26])(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 83093Bromomethyl methyl etherHCID 14255701HCID 14255701, compoundHCID 178418339Butyllithium

Product 1

HCID 14255702HCID 14255702, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 7.14 g of N-t-butyl-2,3-dihydro-2-methylbezo[b]thiophene-7-sulfonamide in 175 ml of dry tetrahydrofuran was added 34 ml of a 1.6M hexane solution of n-butyl lithium at -40° C. to -30° C. under an inert atmosphere. The mixture was allowed to warm and was stirred at room temperature for 30 minutes. It was recooled to -30° C. and was contacted with 2.2 ml of bromomethyl methyl ether. The mixture was allowed to come to room temperature overnight and was acidified with 10 ml of 6N hydrochloric acid. The organic layer was separated, was dried over magnesium sulfate, and was concentrated to give 7.4 g of the title compound as a brown oil.

Workup

  1. temperatureto warm
  2. customwas recooled to -30° C.
  3. waitto come to room temperature overnight
  4. customThe organic layer was separated
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-27ae7c394d244c7d8903131ea8501c01
Source dataset
uspto-grants-1989_11
Patent number
US04878937

Reaction notes

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