tert-Butanol → HCID 178420725, compound

HRID 2406278Notes

Reaction equation

HRID 2406278 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH2:13]1[N:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1>C1(C)C=CC=CC=1>[N+:15]12([S:2]([N-:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])(=[O:4])=[O:3])[CH2:20][CH2:19][N:18]([CH2:17][CH2:16]1)[CH2:13][CH2:14]2.[N:15]12[CH2:20][CH2:19][N:18]([CH2:17][CH2:16]1)[CH2:13][CH2:14]2

Participants

5

Reactant 3

HCID 6386tert-Butanol2×HCID 9237DabcoHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 178420725HCID 178420725, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
3 °C

Procedure

Chlorosulfonyl isocyanate (45.2 Kg, 319.4 mol) was added to toluene (194.2 Kg) and the resulting solution cooled to between about 0-6° C. A solution of tert-butyl alcohol (23.6 Kg, 318.4 mol) in toluene (48.0 Kg) was then added over a period of 90 minutes, maintaining a temperature of between about 0-6° C. The mixture was then stirred until consumption of tert-butyl alcohol was complete (approximately 80 minutes). A solution of triethylenediamine (DABCO, 71.4 Kg, 636.5 mol) in toluene (293.0 Kg) was then added to the mixture over a period of 2.5 hours, maintaining a temperature of between about 0-6° C. The mixture was then warmed to 20-25° C. and stirred for 8 hours. The solid product was isolated by centrifugal filtration under a nitrogen atmosphere and washed with toluene (180.8 Kg) and then tert-butyl methyl ether (51.0 gallons) and spun until no further liquors were seen to be expelled (approximately 60 minutes). The solids were then further dried under vacuum to afford 132.9 Kg of (4-aza-1-azoniabicyclo[2.2.2]oct-1-ylsulfonyl)(tert-butoxycarbonyl)azanide-1,4-diazabicyclo[2.2.2]octane (1:1) hydrochloride.

Workup

  1. temperaturemaintaining a temperature of between about 0-6° C
  2. custom(approximately 80 minutes)
  3. temperaturemaintaining a temperature of between about 0-6° C
  4. temperatureThe mixture was then warmed to 20-25° C.
  5. customThe solid product was isolated by centrifugal filtration under a nitrogen atmosphere
  6. washwashed with toluene (180.8 Kg)
  7. custom(approximately 60 minutes)
  8. customThe solids were then further dried under vacuum

Sources & evidence

ORD record
ord-ceba0231949d416691beff115a29f205
Source dataset
uspto-grants-2014_08
Patent number
US08809356B2

Reaction notes

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