Sulfuryl chloride → HCID 13749915, compound

HRID 979973Notes

Reaction equation

HRID 979973 reaction equation
[C:1]([C:6]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:7]=1[NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([O:3][CH2:4][CH3:5])=[O:2].S(Cl)([Cl:25])(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([C:6]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]([Cl:25])[C:7]=1[NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chloride2×HCID 516892Sodium Bicarbonate2×HCID 13731036HCID 13731036, compound

Product 1

HCID 13749915HCID 13749915, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The chloroform solution of ethyl 2-carboethoxy-3,4-dimethoxybenzenecarbamate prepared in A above was treated with sulfuryl chloride (30.2 g, 0.22 mole) and optionally with sodium bicarbonate (33.3 g, 0.40 mole) and the mixture was stirred at room temperature for 4 hours. An additional charge of sodium bicarbonate (3.3 g, 0.04 mole) and sulfuryl chloride (3.0 g, 0.02 mole) was added and stirring was continued for 16 hours. Filtration and concentration of the filtrate provided crude product as an oil which was crystallized from aqueous methanol. The resultant solid was dissolved in chloroform and the solution was dried, filtered and concentrated to give an oil which was crystallized from hexanes; 37.3 g (85%), mp 111°-113° C.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 16 hours
  4. filtrationFiltration and concentration of the filtrate
  5. customprovided crude product as an oil which
  6. customwas crystallized from aqueous methanol
  7. dissolutionThe resultant solid was dissolved in chloroform
  8. customthe solution was dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oil which
  12. customwas crystallized from hexanes

Sources & evidence

ORD record
ord-c5f7f462cdf7445e9631ecc42896cabd
Source dataset
uspto-grants-1987_01
Patent number
US04634769

Reaction notes

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