Hydrochloric Acid → HCID 14255703, compound

HRID 580252Notes

Reaction equation

HRID 580252 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.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26].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[Si:25]([CH3:28])([CH3:27])[CH3:26])(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 14255701HCID 14255701, compoundHCID 178418339Butyllithium

Product 1

HCID 14255703HCID 14255703, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.0 g of N-t-butyl-2,3-dihydro-2-methylbenzo[b]thiophene-7-sulfonamide in 175 ml of dry tetrahydrofuran was added 20 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 3.0 ml of chlorotrimethylsilane. The mixture was stirred at room temperature for 2 hours and was acidified with 10 ml of 6N hydrochloric acid. The organic layer was separated, was dried over magnesium sulfate, and was concentrated to a crude solid which was suspended in chlorobutane/hexane and filtered to give 2.0 g of the title compound as a beige solid, m.p. 119°-124° C.

Workup

  1. temperatureto warm
  2. customwas recooled to -30° C.
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. customThe organic layer was separated
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationwas concentrated to a crude solid which
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9f955bfe5315408bb94d2854387c4c1b
Source dataset
uspto-grants-1988_06
Patent number
US04752322

Reaction notes

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