Acetonitrile → HCID 20071699, compound

HRID 981067Notes

Reaction equation

HRID 981067 reaction equation
[S:1](=[C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH2:5]1)(=[O:3])=[O:2].[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17].C(#[N:21])C>>[CH2:14]([NH:18][S:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:21])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])=[O:2])[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8007ButylamineHCID 86744574HCID 86744574, compound

Product 1

HCID 20071699HCID 20071699, compoundYield 70%

Procedure

The reaction flask was charged with 10 g (0.039 mole) of 4-(sulfonyl)benzenesulfonyl chloride prepared by a procedure described in J. Med. Chem., 6 pp. 307-11 (1963) in 7 ml acetonitrile. A dropping funnel was charged with 8.8 g (0.12 mole) of butylamine and the amine was added dropwise, allowing the temperature to rise. The mixture was stirred for three hours and then concentrated to a thick residue. The residue was slurried with 100 ml water and the mixture filtered to collect a white solid. After drying, the weight of solid was 8.0 g (70% yield), mp 164°-167° C. A recrystallization from 190 proof ethanol (4 ml/g) and water (4 ml/g) gave 6.6 g of title compound, mp 170°-172° C.

Workup

  1. customprepared by a procedure
  2. concentrationconcentrated to a thick residue
  3. filtrationthe mixture filtered
  4. customto collect a white solid
  5. customAfter drying
  6. customA recrystallization from 190 proof ethanol (4 ml/g) and water (4 ml/g)

Sources & evidence

ORD record
ord-3c4f9f588b9b4c2f8c7d0877271dec05
Source dataset
uspto-grants-1991_02
Patent number
US04990523

Reaction notes

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