Dimethylamine → HCID 20508554, compound

HRID 1758784Notes

Reaction equation

HRID 1758784 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N:19]=[C:20]=[O:21])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:22]=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1.FC1C=CC=CC=1[C:32]1C2C=C(NC(NCCO)=O)C=CC=2N2C=NN=C2[CH2:34][N:33]=1.NC1C=CC2N3C=NN=C3CN=C(C3C=CC=CC=3Cl)C=2C=1.C(=O)([O-])[O-].[Na+].[Na+].CNC>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][C:20](=[O:21])[N:33]([CH3:34])[CH3:32])[CH:17]=[CH:18][C:13]=2[N:12]2[CH:22]=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 20508545HCID 20508545, compoundHCID 20508551HCID 20508551, compoundHCID 20508564HCID 20508564, compound

Product 1

HCID 20508554HCID 20508554, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]isocyanate, prepared as described in paragraph (a) of Example 1 from 7.0 g (22.6 mmol) of 8-amino-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine, but using methylene chloride in place of 1,2-dichloroethane, is added in one portion while cooling with ice and stirring a suspension of 8.7 g (81.9 mmol) of sodium carbonate in 5.3 g (117.8 mmol) of dimethylamine and 50 ml of 1,2-dichloroethane. The mixture is left for 25 hours at room temperature and then evaporated at 50° C. in vacuo. The residue is suspended in 300 ml of water, extracted four times with methylene chloride/ethanol (4:1) and the combined organic extracts are subsequently dried and evaporated. Crystallisation from methylene chloride/ethyl acetate yields 3-[6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-1,1-dimethylurea of melting point 180° C. (decomposition).

Workup

  1. additionis added in one portion
  2. temperaturewhile cooling with ice
  3. customevaporated at 50° C. in vacuo
  4. extractionextracted four times with methylene chloride/ethanol (4:1)
  5. customthe combined organic extracts are subsequently dried
  6. customevaporated
  7. customCrystallisation from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-caed810669f44d5e8a9b781b1d67cbdd
Source dataset
uspto-grants-1983_02
Patent number
US04374773

Reaction notes

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