Acetyl chloride → HCID 19093737, compound

HRID 487405Notes

Reaction equation

HRID 487405 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:32])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH3:2].[C:33]([Cl:36])(=[O:35])[CH3:34]>C(O)(=O)C>[ClH:36].[C:33]([NH:31][S:28]([C:23]1[C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][N:8]3[C:9]4[C:4](=[C:3]([CH2:1][CH3:2])[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=4)[CH:5]=[CH:6][C:7]3=[O:32])=[CH:17][CH:18]=2)=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:29])=[O:30])(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 19093708HCID 19093708, compound

Product 1

HCID 19093737HCID 19093737, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide (250 mg), acetyl chloride (2 ml) and acetic acid (1 ml) was heated at reflux for 4 hours. The mixture was then concentrated by evaporation and the residue was purified by repeated precipitation from ethanol solution by the addition of ether to give N-acetyl-4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide hydrochloride as an amorphous solid (153 mg); NMR (d6 -DMSO): 1.27(t, 3H), 1.31(t, 2H), 1.69(s, 3H), 2.99(q, 2H), 3.36(q, 2H), 5.63(s, 2H), 6.98(d, 1H), 7.2-7.4(complex m, 5H), 7.5-7.8(m, 3H), 8.06(dd, 1H), 8.40(d, 1H), 11.53(s, 1H); mass spectrum (+ve FAB, methanol/NBA): 490 (M+H)+ ; microanalysis, found: C, 59.9; H, 5.4; N, 7.7%; C27H27N3O4S.HCl.H2O requires: C, 59.6; H, 5.5; N, 7.7%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe mixture was then concentrated by evaporation
  4. customthe residue was purified
  5. customprecipitation from ethanol solution
  6. additionby the addition of ether

Sources & evidence

ORD record
ord-e2ec349e793f4120bc7e86adca93fea2
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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