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

HRID 1589324Notes

Reaction equation

HRID 1589324 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 731849592-Chloroethyl 2-chloro-N-hydroxybenzenecarboximidothioate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-dfbbfb36bfe140b3a0771f2882e630ec
Source dataset
uspto-grants-1986_02
Patent number
US04569690

Reaction notes

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