Dimethyl Sulfide → HCID 15631820, compound

HRID 2351887Notes

Reaction equation

HRID 2351887 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][S:12][CH3:13].ClN1C(=O)CCC1=O.[OH-].[Na+]>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[C:3]([NH2:4])=[C:5]([CH2:11][S:12][CH3:13])[C:6]([F:10])=[C:7]([F:9])[CH:8]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 112065582-Bromo-4,5-difluoroaniline

Product 1

HCID 15631820HCID 15631820, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-bromo-4,5-difluoroaniline (100 g) and dimethyl sulfide (49 ml) in anhydrous dichloromethane (1.2 liter) is added gradually N-chlorosuccinimide (90 g) at below 15° C., and thereafter is further added in portions triethylamine (93 ml) at 15° C. After the addition, the mixture is refluxed for 7 hours. After cooling, 10% aqueous sodium hydroxide (one liter) is added to the reaction mixture, and the mixture is extracted with dichloromethane. The extract is dried over magnesium sulfate and concentrated, and the resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:n-hexane=1:2). The product is recrystallized from n-hexane to give 6-bromo-3,4-difluoro-2-methylthiomethylaniline (52 g) as a white crystal, m.p. 60°-61° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed for 7 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe extract is dried over magnesium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue is purified by silica gel column chromatography (solvent, dichloromethane:n-hexane=1:2)
  8. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-136d42fbad774c7aa02e192dd2b65644
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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