Dimethyl Sulfide → HCID 18950256, compound

HRID 1492387Notes

Reaction equation

HRID 1492387 reaction equation
ClN1C(=O)CCC1=O.[NH2:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH3:22][S:23][CH3:24].C(N(CC)CC)C>ClCCl>[NH2:9][C:10]1[C:11]([CH2:22][S:23][CH3:24])=[C:12]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 1068Dimethyl Sulfide2×HCID 8471Triethylamine3×HCID 31398Chlorosuccinimide2×HCID 18950325HCID 18950325, compound

Product 1

HCID 18950256HCID 18950256, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-chlorosuccinimide (215 g) was added during 10 minutes to a solution containing ethyl 3-amino-4-chlorobenzoate (108 g) and dimethyl sulphide (117 ml) in dichloromethane maintaining below 0° C. Triethylamine (80 ml) was added and after 20 minutes further additions of dimethyl sulphide (117 ml), N-chlorosuccinimide (215 g) and triethylamine (80 ml) were made. After 0.5 hours additional triethylamine (280 ml) was introduced, the mixture heated under reflux conditions overnight and evaporated. Ether was added and this was washed with water, dilute sodium bicarbonate, dried (magnesium sulphate) and evaporated. Purification by chromatography, eluting with ethyl acetate/petroleum ether gave ethyl 3-amino-4-chloro-2-methylsulphenylmethylbenzoate (47.6 g), NMR (CDCl3) 1.45 (t,3H), 2.1 (s,3H), 4.1 (s,2H), 4.3 (q,2H), 4.7 (s,2H), 7.2 (m,2H).

Workup

  1. temperaturethe mixture heated under reflux conditions overnight
  2. customevaporated
  3. additionEther was added
  4. washthis was washed with water, dilute sodium bicarbonate
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customPurification by chromatography
  8. washeluting with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3e96eeed242a4780828c038b0417b2da
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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