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Dimethylamine → HCID 19819744, compound

HRID 1031179
Notes
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Reaction equation

HRID 1031179 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH2:5][CH2:6][CH:7]1[N:20]([CH3:21])[C:12]2=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]2[C:10](=[O:22])[N:9]([CH3:23])[CH2:8]1>CO>[OH2:22].[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][CH:7]1[N:20]([CH3:21])[C:12]2=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]2[C:10](=[O:22])[N:9]([CH3:23])[CH2:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Product 1

HCID 19819744HCID 19819744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 90 mL of freshly collected dimethylamine and 10 mL of methanol was added 3.25 g (0.011 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one. The reaction flask was sealed and left standing at room temperature for 6 days. The dimethylamine was then allowed to evaporate at room temperature and the residue partitioned between 75 mL of 1N NaOH and 75 mL of CH2Cl2. The organic phase was washed with another 50 mL of 1N NaOH. The combined organic layers were dried over Na2SO4, filtered, and concentrated by rotary evaporation. The solid residue was recrystallized from isopropyl ether to give 2.8 g of white analytically pure crystals, mp 91°-95° C.

Workup

  1. customThe reaction flask was sealed
  2. waitleft
  3. customto evaporate at room temperature
  4. customthe residue partitioned between 75 mL of 1N NaOH and 75 mL of CH2Cl2
  5. washThe organic phase was washed with another 50 mL of 1N NaOH
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe solid residue was recrystallized from isopropyl ether
  10. customto give 2.8 g of white analytically pure crystals, mp 91°-95° C.

Sources & evidence

ORD record
ord-faa5d8b0e54c4a86a33383a9ef172c15
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05109013

Reaction notes

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