Triethylamine → HCID 67856746, compound

HRID 484430Notes

Reaction equation

HRID 484430 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C@@H:5]([C:15]([O:17][CH3:18])=[O:16])[CH2:4]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[Cl:13][C:11]1[CH:10]=[C:9]([Cl:14])[CH:8]=[C:7]2[C:12]=1[C@@H:3]([NH:2][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:4][C@H:5]([C:15]([O:17][CH3:18])=[O:16])[NH:6]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 67690826HCID 67690826, compound

Product 1

HCID 67856746HCID 67856746, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.15 g, 0.482 mmol) in dichloromethane (15 ml) was added triethylamine (0.14 ml, 1.01 mmol) and the mixture was stirred under an atmosphere of nitrogen at room temperature until dissolution was complete. To this solution was added methanesulphonyl chloride (0.039 ml, 0.50 mmol) and the resulting mixture was stirred at room temperature under an atmosphere of nitrogen for 2.5 h. A further portion of methanesulphonyl chloride (0.039 ml, 0.50 mmol) was added and stirring was continued for 2 h after which time more triethylamine (0.07 ml, 0.50 mmol) was added and the mixture was stirred for a further 18 hours. The solvent was removed in vacuo and the residue obtained was partitioned between dilute citric acid solution (50 ml) and ethyl acetate (100 ml). The organic layer was washed with saturated sodium hydrogen carbonate (2×50 ml), brine (1×50 ml), dried (MgSO4) and evaporated to give the title compound as colourless crystals (0.14 g, m.p. 143°-146° C.); δ (250 MHz, CDCl3) 1.69 (1H, m, CHACHBHCCHD), 2.90 (1H, dm, J=13.6 Hz, CHACHBHCCHD), 3.17 (3H, s, --SO2CH3), 3.83 3H, s, CO2CH3), 4.26 (2H, m, CHACHBHCCHD) and CHNHSO2CH3), 4.84 (1H, m, CHACHBHCCHD), 6.57 (1H, d, J=1.9 Hz, 6-H or 8-H), 6.73 (1H, d, J=1.9 Hz, 6-H or 8-H); m/e 353 (M+), 198 (100% M-NHSO2CH3, CO2CH3 and H).

Workup

  1. stirringthe resulting mixture was stirred at room temperature under an atmosphere of nitrogen for 2.5 h
  2. stirringstirring
  3. stirringthe mixture was stirred for a further 18 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue obtained
  6. customwas partitioned between dilute citric acid solution (50 ml) and ethyl acetate (100 ml)
  7. washThe organic layer was washed with saturated sodium hydrogen carbonate (2×50 ml), brine (1×50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-a1d121534dd84fea9764374b43ccad86
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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