Triethylamine → HCID 42603194, compound

HRID 659040Notes

Reaction equation

HRID 659040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[C:15]1[NH:19][N:18]=[N:17][N:16]=1.C(N(CC)CC)C.Cl[CH2:28][C:29]1[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=1>CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[C:15]1[N:19]([CH2:28][C:29]2[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=2)[N:18]=[N:17][N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7365362-(chloromethyl)-1-methyl-1H-imidazole2×HCID 178486844HCID 178486844, compound

Product 1

HCID 42603194HCID 42603194, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
27.5 °C

Procedure

Experimental Procedure: 50.0 ml of N,N-dimethyl acetamide and 5.0 g (0.019 mol) of 6,7-dimethoxy-4-(1H-tetrazol-5-yl)quinazoline were charged into a 250 ml of 4necked round bottom flask, connected to a mechanical stirrer, thermometer socket, condenser and addition flask under mild nitrogen atmosphere. 3.80 g (0.038 mol) of triethyl amine was added at 25-30° C. Stirred the mass for 15-20 min at 25-30° C. Reaction mass temperature was raised to 50-55° C. Maintained the mass temperature at 50-55° C. for 15-20 min. 2-chloro methyl -1-methyl-imidazole solution [2.50 g (0.019 mol) 2-chloro methyl -1-methyl-imidazole was dissolved in 25.0 ml of N,N-dimethyl acetamide] was added slowly at 50-55° C. for 30-45 min. Maintained the mass temperature at 50-55° C. for 15-20 min. Raised the mass temperature to 80-85° C. Maintained the mass temperature at 80-85° C. for 7-8 hours. N,N-dimethyl acetamide was completely distilled under vacuum. Crude compound was purified by the column chromatography by using hexane and ethyl acetate. Obtained pure compound weight 2.40 g (yield 35.2% by theory).

Workup

  1. customconnected to a mechanical stirrer
  2. additionthermometer socket, condenser and addition flask under mild nitrogen atmosphere
  3. customReaction mass temperature
  4. temperaturewas raised to 50-55° C
  5. temperatureMaintained the mass temperature at 50-55° C. for 15-20 min
  6. temperatureMaintained the mass temperature at 50-55° C. for 15-20 min
  7. temperatureRaised the mass temperature to 80-85° C
  8. temperatureMaintained the mass temperature at 80-85° C. for 7-8 hours
  9. distillationN,N-dimethyl acetamide was completely distilled under vacuum
  10. customCrude compound was purified by the column chromatography
  11. customObtained pure compound weight 2.40 g (yield 35.2% by theory)

Sources & evidence

ORD record
ord-be1391933c1b4566bf4e71f1f77b47d3
Source dataset
uspto-grants-2011_12
Patent number
US08080558B2

Reaction notes

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