Triethylamine → HCID 3460293, compound

HRID 886776Notes

Reaction equation

HRID 886776 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(N(CC)CC)C.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[S:29](Cl)(=[O:31])=[O:30])[CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:29]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:28]=2[N:19]=[CH:20][CH:21]=[CH:22]3)(=[O:30])=[O:31])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 292208-Quinolinesulfonyl chloride

Product 1

HCID 3460293HCID 3460293, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
65 °C

Procedure

The product has already been described in: V. M. Dziomko et al., Azotsoderzhashchie Geterotsikly 1967, 281-284; but by a different method of synthesis. Several grains of activated 4 Å molecular sieve are added to a solution under argon of 8-aminoquinoline (200 mg; 1.39 mmol) and triethylamine (0.30 ml; 2.15 mmol) in 10 ml of CHCl3 and the mixture is stirred slowly for 1 hour. 8-quinolinesulfonyl chloride (350 mg; 1.54 mmol) is added and the mixture is heated to 65° C. for 15 hours. After cooling, 50 ml of CHCl3 are added and the mixture is washed in water (2×50 ml) then dried over anhydrous Na2SO4 and the solvent is evaporated under reduced pressure. The solid is washed with 5 ml of CH2Cl2 to yield after drying 25 in the form of a beige powder (108 mg; 0.32 mmol, yield=23%). NMR-1H (250 MHz, DMSO-d6) δ, ppm: 10.44 (s, 1H); 9.11 (dd, 3J (H, H)=4.5 Hz, 4J (H, H)=1.5 Hz, 1H); 8.83 (dd, 3J (H, H)=4.0 Hz, 4J (H, H)=1.5 Hz, 1H); 8.47 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 8.40 (dd, 3J (H, H)=8.5 Hz, 4J (H, H)=1.5 Hz, 1H); 8.22 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 8.20 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 7.80 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 7.70 (dd, 3J (H, H)=8.0 and 7.5 Hz, 1H); 7.62 (dd, 3J (H, H)=8.5 and 4.5 Hz, 1H); 7.51 ((dd, 3J (H, H)=8.5 and 4.0 Hz, 1H); 7.50 (dd, 3J (H, H)=8.5 Hz, 4J (H, H)=1.0 Hz, 1H); 7.42 (dd, 3J (H, H)=8.0 and 7.5 Hz, 1H). NMR-13C (63 MHz, DMSO-d6) δ, ppm: 151.5 (CH); 148.9 (CH); 142.1 (Cq); 137.6 (Cq); 136.9 (CH); 136.3 (CH); 134.4 (CH); 134.2 (Cq); 133.7 (Cq); 131.7 (CH); 128.2 (Cq); 127.8 (Cq); 126.6 (CH); 125.5 (CH); 122.6 (CH); 122.3 (CH); 122.1 (CH); 113.8 (CH). MS (CID, NH3): m/z=336 (MH+). Analysis (%) for C18H13N3O2S.0.2H2O: calculated C, 63.78. H, 3.98. N, 12.40. found C, 63.53. H, 3.70. N, 12.23.

Workup

  1. custombut by a different method of synthesis
  2. temperatureAfter cooling
  3. washthe mixture is washed in water (2×50 ml)
  4. dry with materialthen dried over anhydrous Na2SO4
  5. customthe solvent is evaporated under reduced pressure
  6. washThe solid is washed with 5 ml of CH2Cl2
  7. customto yield
  8. customafter drying 25 in the form of a beige powder (108 mg; 0.32 mmol, yield=23%)

Sources & evidence

ORD record
ord-8abe8445b2124ecd80b45ec3435abded
Source dataset
uspto-grants-2012_08
Patent number
US08247396B2

Reaction notes

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