Hydrochloric Acid → HCID 14948427, compound

HRID 2398431Notes

Reaction equation

HRID 2398431 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1N.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].C(OC([S-])=[S:25])C.[K+].[OH-].[K+]>O.C(O)C.C(Cl)Cl>[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[SH:25]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 754606-Chloro-m-anisidineHCID 517045Sodium AcetateHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 14948427HCID 14948427, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 450 ml of concentrated hydrochloric acid and 1,200 ml of water is added to 157.6 g of 2-chloro-5-methoxy-aniline, while stirring, and the mixture is diazotised with a solution of 69 g of NaNO2 in 130 ml of water at 0°-5°. The mixture is then buffered with sodium acetate and the diazonium salt solution is added dropwise, while stirring, to a solution, at 70°, of 256 g of potassium ethylxanthate in 360 ml of water. After cooling, the mixture is worked up with CH2Cl2 and the resulting crude xanthic acid ester is saponified with KOH in ethanol and the mixture is evaporated, acidified and distilled with steam to give 2-chloro-5-methoxy-thiophenol; b.p. 110°/0.5 mm.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is evaporated
  3. distillationdistilled with steam

Sources & evidence

ORD record
ord-e5d4ec4bcf324b13ac8e951bc8530ac1
Source dataset
uspto-grants-1977_05
Patent number
US04024272

Reaction notes

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