Bromomethyl 4-methoxyphenyl ketone → HCID 20485508, compound

HRID 647136Notes

Reaction equation

HRID 647136 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:11][S:10][C:9](=[S:12])[CH:8]=2)[CH2:3][CH2:2]1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=[O:22])[CH2:20]Br)=[CH:17][CH:16]=1.[I-:25].[Na+]>CC(C)=O.C(Cl)Cl>[I-:25].[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=[O:22])[CH2:20][S:12][C:9]2[S:10][S:11][C:7](=[N+:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 5238Sodium IodideHCID 12863631HCID 12863631, compound

Product 1

HCID 20485508HCID 20485508, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 5-morpholino-1,2-dithiol-3-thione (2.62 g), 4-methoxyphenacyl bromide (4.12 g) and sodium iodide (3 g) in acetone (60 cc) is heated to the reflux temperature and maintained there for 2 hours. After cooling to a temperature of about 20° C., the insoluble product is filtered off and washed successively with acetone (30 cc), distilled water (2×40 cc) and acetone (2×30 cc). The product thus obtained is suspended in methylene chloride (110 cc). After stirring for 1 hour at a temperature of about 20° C., the insoluble product is separated by filtration. N-[5-(4-Methoxyphenacylthio)-1,2-dithiol-3-ylidene]-morpholinium iodide, melting at 152°-155° C., is thus obtained.

Workup

  1. temperatureis heated to the reflux temperature
  2. temperaturemaintained there for 2 hours
  3. filtrationthe insoluble product is filtered off
  4. washwashed successively with acetone (30 cc)
  5. distillationdistilled water (2×40 cc) and acetone (2×30 cc)
  6. customThe product thus obtained
  7. customthe insoluble product is separated by filtration

Sources & evidence

ORD record
ord-71e395ea46854b6b8a86782c7fe69491
Source dataset
uspto-grants-1983_10
Patent number
US04407797

Reaction notes

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