Thiophosgene → HCID 13563671, compound

HRID 979720Notes

Reaction equation

HRID 979720 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[Cl:11])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)([Cl:15])=[S:14].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:13]([O:12][C:7]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[S:14]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 10910230HCID 10910230, compound

Product 1

HCID 13563671HCID 13563671, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 50 ml of chloroform were dissolved 9.2 g of 3-tert-butyl-4-chlorophenol and 6.3 g of thiophosgene, and 60 ml of 1N-sodium hydroxide solution were added dropwise thereto with stirring at room temperature. After completion of this dropwise addition, the mixture was subjected to stirring over a period of 3 hours. From the reaction mixture was separated chloroform layer, which was thereafter dried over anhydrous calcium chloride. Then, chloroform was distilled off and the residue was distilled under reduced pressure to give 9.5 g of O-3-tert-butyl-4-chlorophenyl chlorothioformate having boiling point of 103°-106° C./0.5 mmHg, of which properties are as follows.

Workup

  1. additionwere added dropwise
  2. additionAfter completion of this dropwise addition
  3. stirringto stirring over a period of 3 hours
  4. customFrom the reaction mixture was separated chloroform layer, which
  5. dry with materialwas thereafter dried over anhydrous calcium chloride
  6. distillationThen, chloroform was distilled off
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7e9adeac2b2140798021751f2df1614a
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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