Chloroacetic Acid → HCID 86739047, compound

HRID 647131Notes

Reaction equation

HRID 647131 reaction equation
[C:1]1([NH:7][C:8]2[S:12][S:11][C:10](=[S:13])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:15][C:16]([OH:18])=[O:17].[I-:19].[Na+]>CC(C)=O>[IH:19].[C:1]1([N:7]=[C:8]2[CH:9]=[C:10]([S:13][CH2:15][C:16]([OH:18])=[O:17])[S:11][S:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 5238Sodium IodideHCID 13150961HCID 13150961, compound

Product 1

HCID 86739047HCID 86739047, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 5-phenylamino-1,2-dithiol-3-thione (9 g), chloroacetic acid (4.15 g) and sodium iodide (6.6 g) in acetone (135 cc) is heated under reflux for 35 minutes. After cooling to a temperature of about 20° C., the insoluble product is filtered off and washed successively with acetone (3×15 cc), with water (3×10 cc) and then with acetone (3×10 cc). By recrystallisation of this crude product from methanol (470 cc), (3-phenylimino-1,2-dithiol-5-ylthio)-acetic acid hydroiodide (7.1 g) is obtained, melting at about 205° C. with decomposition.

Workup

  1. temperatureunder reflux for 35 minutes
  2. filtrationthe insoluble product is filtered off
  3. washwashed successively with acetone (3×15 cc), with water (3×10 cc)
  4. customBy recrystallisation of this crude product from methanol (470 cc)

Sources & evidence

ORD record
ord-d17875c9bd8144369fbf6a9a18276b1c
Source dataset
uspto-grants-1983_10
Patent number
US04407797

Reaction notes

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