Ammonium Chloride → HCID 18960407, compound

HRID 1707933Notes

Reaction equation

[CH3:1][C:2]([NH:5][S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]#[C-:17])(=[O:8])=[O:7])([CH3:4])[CH3:3].O1CCCC1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1.C1CCCCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:16][CH:17]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 25.2 g (0.10 mol) of N-(1,1-dimethylethyl)-2-isocyanobenzenemethanesulfonamide in 600 mL anhydrous THF was cooled to -70° C. under nitrogen atmosphere and treated with 147 mL (0.22 mol) 1.5M lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane at such a rate as to keep the temperature under -60° C. The mixture was stirred at -70° C. for 15 minutes then warmed to 0° C. Saturated ammonium chloride solution (75 mL) was then added and the product was extracted with two 200 mL portions of ethyl acetate. The organic extract was washed with 10% HCl, brine, dried (MgSO4) and evaporated in vacuo. The resulting residue was triturated with ether/n-butyl chloride and collected by filtration to afford 22.7 g of the title compound, m.p. 157°-158° C.

Workup

customunder -60° C
temperaturethen warmed to 0° C
extractionthe product was extracted with two 200 mL portions of ethyl acetate
extractionThe organic extract
washwas washed with 10% HCl, brine
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe resulting residue was triturated with ether/n-butyl chloride
filtrationcollected by filtration

Sources & evidence

ORD record: ord-2ac12c1408e44856888b5c8eb26a5730
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356862

Reaction notes

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