Dimethyl Sulfoxide → HCID 11252373, compound

HRID 1683430Notes

Reaction equation

HRID 1683430 reaction equation
[Cl-].[Na+].C(CC[CH:8]([CH:14]([C:19]#[N:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(O)=O.CS(C)=O>O.C(OC)(C)(C)C>[C:19]([CH:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:20]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 86583641HCID 86583641, compound

Product 1

HCID 11252373HCID 11252373, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

An 800 L still was charged with sodium chloride (21 kg, 359 mol), 2-carboxyethyl-3-cyano-5-methylhexanoic acid, ethyl ester (80.0 kg, 313 mol), dimethylsulfoxide (238 kg), and water (10.8 kg, 600 mol). The mixture was heated to 137°-148° C. for 8.5 hours. The mixture was cooled to below 50° C., and treated with methyl tert-butyl ether (125 kg). The mixture was cooled to 0°-10° C., and treated with water (160 L) in portions to maintain the temperature below 40° C. After stirring for 15-30 minutes, the phases were separated. The aqueous phase was extracted with methyl tert-butyl ether (125 kg). The organic extracts were combined with a vessel rinse (25 kg methyl tert-butyl ether) and was extracted with water (110 L). The water phase was discarded. The methyl tert-butyl ether phase was concentrated by atmospheric pressure distillation to a batch temperature of about 65° C. The batch was cooled to 30°-40° C. and further concentrated by vacuum distillation until the solvent content was acceptable (<5% methyl tert-butyl ether by area %GC analysis). The product was obtained as a brown oil (51.3 kg, 85.7%).

Workup

  1. temperatureThe mixture was heated to 137°-148° C. for 8.5 hours
  2. temperatureThe mixture was cooled to below 50° C.
  3. temperatureThe mixture was cooled to 0°-10° C.
  4. temperatureto maintain the temperature below 40° C
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with methyl tert-butyl ether (125 kg)
  7. customThe organic extracts were combined with a vessel
  8. washrinse (25 kg methyl tert-butyl ether)
  9. extractionwas extracted with water (110 L)
  10. concentrationThe methyl tert-butyl ether phase was concentrated by atmospheric pressure distillation to a batch temperature of about 65° C
  11. temperatureThe batch was cooled to 30°-40° C.
  12. concentrationfurther concentrated by vacuum distillation until the solvent content

Sources & evidence

ORD record
ord-4501c959a44b42f8b18f807b409f0aac
Source dataset
uspto-grants-1997_06
Patent number
US05637767

Reaction notes

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