Water → HCID 13686308, compound

HRID 1905339Notes

Reaction equation

HRID 1905339 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:23]=[O:24].O>C1COCC1.CCOCC.CCCCCC>[C:1]([N:5]1[CH:23]([OH:24])[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=2[S:6]1(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 793248HCID 793248, compoundHCID 178418339Butyllithium

Product 1

HCID 13686308HCID 13686308, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 49.5 g of N-t-butyl-2-chlorobenzenesulfonamide in 875 mls of dry THF was added 262 ml of a 1.6M hexane solution of n-butyl lithium at -20° to -5° C. under an inert atmosphere. The mixture was stirred at 0° C. for 1 hour, room temperature for 2 hours, recooled to -78° C. and contacted with 38 mls of dry dimethylformamide. The mixture was allowed to warm to room temperature overnight, poured into water, acidified to a ph of ~3 and ether extracted. The extract was washed with water and brine, dried over MgSO4 and concentrated to give a yellow oil. The oil was dissolved in 50% ether in hexane solution and allowed to stand, giving, after filtration, 38 g of the title compound as colorless crystals, m.p. 139°-141° C.

Workup

  1. customrecooled to -78° C.
  2. temperatureto warm to room temperature overnight
  3. extractionextracted
  4. washThe extract was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customgiving
  9. filtrationafter filtration, 38 g of the title compound as colorless crystals, m.p. 139°-141° C.

Sources & evidence

ORD record
ord-9d385fd7b16e40d6a71e3d9d6da1b0ef
Source dataset
uspto-grants-1989_06
Patent number
US04842639

Reaction notes

Loading…