Dimethylamine → HCID 14373876, compound

HRID 1841826Notes

Reaction equation

HRID 1841826 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].S(=O)(=O)(O)O.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][CH:16]=[CH:15]2.[Cl-].[Na+]>CN(C=O)C.O>[CH3:3][N:4]([CH2:1][C:15]1[C:14]2[C:18](=[CH:19][C:20]([Cl:21])=[C:12]([Cl:11])[CH:13]=2)[NH:17][CH:16]=1)[CH3:5]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 104877765,6-dichloro-1H-indole

Product 1

HCID 14373876HCID 14373876, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

19.6 kg of 37% aqueous formaldehyde solution and 16.3 kg of DMF were added to a reactor and then the reactor was cooled to 5° C. 33.3 kg of 33% aqueous dimethylamine solution was added. The reaction mixture was stirred for an additional hour at 0-5° C. upon completion of addition. 11.8 kg of concentrated sulfuric acid was added slowly to the mixture while the temperature was maintained below 10° C. The mixture was stirred for an additional 15 minutes and cooled to 5° C. A solution of 30 kg of 5,6-dichloroindole in 30 kg of DMF was added slowly to the reactor and stirred for an additional hour at 5° C. The mixture was allowed to warm to room temperature and stirred for 24 hrs. The mixture was then added to a reactor containing a solution of 50 kg industrial sodium chloride in 1600 L water. To this reactor was added 10 kg activated carbon and the mixture stirred for 30 minutes. Upon filtration, the filtrate was adjusted to pH>12 with 20% aqueous sodium hydroxide solution. The precipitate was filtered, washed with water until pH=7-8, centrifuged, and dried to yield crude 35 kg 5,6-dichlorogramine. Recrystallization in 70% ethanol produced the pure product with melting point of 150-154° C.

Workup

  1. temperaturewas maintained below 10° C
  2. stirringThe mixture was stirred for an additional 15 minutes
  3. temperaturecooled to 5° C
  4. stirringstirred for an additional hour at 5° C
  5. temperatureto warm to room temperature
  6. stirringstirred for 24 hrs
  7. additionThe mixture was then added to a reactor
  8. additionTo this reactor was added 10 kg
  9. stirringthe mixture stirred for 30 minutes
  10. filtrationUpon filtration
  11. filtrationThe precipitate was filtered
  12. washwashed with water until pH=7-8
  13. customcentrifuged, and dried

Sources & evidence

ORD record
ord-031bc967985447a4bed3c0aed46b9bae
Source dataset
uspto-grants-2015_02
Patent number
US08945397B2

Reaction notes

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