Ammonia → HCID 362687, compound

HRID 2306070Notes

Reaction equation

HRID 2306070 reaction equation
[C@:1]12([CH2:11][S:12]([OH:15])(=O)=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=O.S(Cl)(Cl)=O.[NH3:20]>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:9][C:8]1([CH3:10])[CH:5]2[CH2:6][CH2:7][C:1]31[C:2]([CH2:4]2)=[N:20][S:12](=[O:15])(=[O:13])[CH2:11]3

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 218580(1S)-(+)-Camphor-10-sulphonic acid

Product 1

HCID 362687HCID 362687, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent3×

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide (230 g) and (1S)-(+)-10-camphorsulfonic acid (190 kg, 818 mol) were added to toluene (190 L), and thionyl chloride (116.8 kg, 982 mol) was added in a thin stream at 70° C.-80° C. over 2 h, and the mixture was stirred at the same temperature for 2 h. The obtained solution of camphorsulfonyl chloride in toluene was added dropwise at −10° C. to 25° C. over 3 h to a mixture of 28 wt % aqueous ammonia (248.7 kg, 4.1 kmol) and toluene (277 L), which mixture had been separately prepared and cooled to −10° C. to −5° C. The container of acid chloride was washed with toluene (29 L) and the washing was added to the reaction mixture, which was followed by stirring at 10° C.-25° C. for 2 h. The reaction mixture was heated to 80° C. over 85 min and stirred at 80° C.-83.3° C. for 3 h. The amount of the ammonia gas generated was 39 m3. The reaction mixture was cooled to 60° C. over 20 min and aged at 54° C.-60° C. for 15 min. The reaction mixture was cooled to 20° C. over 1 h and stirred at 15° C.-20° C. for 40 min. The reaction mixture was filtered at 15° C. and washed successively with toluene (57 L) and water (380 kg) to give wet crystals (177.1 kg). The crystals were partially dried and analyzed. As a result, the crystals contained the title compound in an amount of 144.7 kg (yield 83%).

Workup

  1. additionwas added in a thin stream at 70° C.-80° C. over 2 h
  2. customhad been separately prepared
  3. temperaturecooled to −10° C. to −5° C
  4. washThe container of acid chloride was washed with toluene (29 L)
  5. additionthe washing was added to the reaction mixture, which
  6. stirringby stirring at 10° C.-25° C. for 2 h
  7. stirringstirred at 80° C.-83.3° C. for 3 h
  8. temperatureThe reaction mixture was cooled to 60° C. over 20 min
  9. waitaged at 54° C.-60° C. for 15 min
  10. temperatureThe reaction mixture was cooled to 20° C. over 1 h
  11. stirringstirred at 15° C.-20° C. for 40 min
  12. filtrationThe reaction mixture was filtered at 15° C.
  13. washwashed successively with toluene (57 L) and water (380 kg)

Sources & evidence

ORD record
ord-50e5b9119fc84409924498330cf1db58
Source dataset
uspto-grants-2002_08
Patent number
US06441187B1

Reaction notes

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