Water → 2-Chloroethyl 2-chloro-N-hydroxybenzenecarboximidothioate

HRID 653005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653005
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].C(N(CC)CC)C.[Cl:18][CH2:19][CH2:20][SH:21].O>C(Cl)(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([S:21][CH2:20][CH2:19][Cl:18])=[N:5][OH:6]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 78022Ethanethiol, 2-chloro-HCID 96239o-Chlorobenzaldoxime

Produkt 1

HCID 731849592-Chloroethyl 2-chloro-N-hydroxybenzenecarboximidothioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Chlorobenzaldoxime (46.7 g, 0.3 mol) in chloroform (350 ml) was cooled and stirred in an ice/salt bath. Chlorine gas was bubbled into the reaction until an excess was present. Excess chlorine and solvent were removed and the remaining 2-chloro-N-hydroxybenzenecarboximidoyl chloride dissolved in ether (250 ml). Solutions of triethylamine (30.3 g, 0.3 mol) in ether (50 ml) and 2-chloroethanethiol (29 g, 0.3 mol) in ether (50 ml) were added simultaneously with stirring and cooling. After the addition, the reaction was allowed to warm to room temperature and left overnight. Water was added, and the ether layer was washed with additional water, then dried with anhydrous magnesium sulphate. Evaporation left a white solid, 2-chloroethyl 2-chloro-N-hydroxybenzenecarboximidothioate, m.p. 115°-117° C., (Found: C, 43.29; H, 3.58; N, 5.59. C9H9Cl2NOS requires C, 43.21; H, 3.62; N, 5.60).

Aufarbeitung

  1. customChlorine gas was bubbled into the reaction until
  2. customExcess chlorine and solvent were removed
  3. dissolutionthe remaining 2-chloro-N-hydroxybenzenecarboximidoyl chloride dissolved in ether (250 ml)
  4. stirringwith stirring
  5. temperaturecooling
  6. additionAfter the addition
  7. washthe ether layer was washed with additional water
  8. dry with materialdried with anhydrous magnesium sulphate
  9. customEvaporation
  10. waitleft a white solid, 2-chloroethyl 2-chloro-N-hydroxybenzenecarboximidothioate, m.p. 115°-117° C., (Found: C, 43.29; H, 3.58; N, 5.59. C9H9Cl2NOS requires C, 43.21; H, 3.62; N, 5.60)

Quellen und Nachweise

ORD-Eintrag
ord-5604cb1c320e49fcaabd983b04feefc9
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675044

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