Ethyl Acetate → HCID 86620262, compound

HRID 2238441Notes

Reaction equation

HRID 2238441 reaction equation
C([N:8](CC1C=CC=CC=1)[S:9]([C:12]1[CH:13]=[CH:14][C:15]2[CH:23]=[CH:22][C:21]3[N:20]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:19][CH:18](CCl)[C:17]=3[C:16]=2[CH:32]=1)(=[O:11])=[O:10])C1C=CC=CC=1.CCOC(C)=O>OS(O)(=O)=O>[F:28][C:25]([F:26])([F:27])[C:24]([N:20]1[C:21]2[CH:22]=[CH:23][C:15]3[CH:14]=[CH:13][C:12]([S:9]([NH2:8])(=[O:10])=[O:11])=[CH:32][C:16]=3[C:17]=2[CH2:18][CH2:19]1)=[O:29]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86620261HCID 86620261, compound

Product 1

HCID 86620262HCID 86620262, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Sulfonamide 215 (750 mg, 1.31 mmol) was cooled to 0° C., dissolved in conc. H2SO4 (20 mL) at 0° C., and the solution was stirred at this temperature for 2 h. Ice water and EtOAc were added and the mixture was extracted with EtOAc (×3). The combined extracts were washed with brine (×3), dried, and evaporated to give 1-chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-8-sulfonamide (216) (490 mg, 96%). A sample was recrystallised from CH2Cl2/EtOAc as yellow crystals: mp 229-231° C.; 1H NMR [(CD3)2SO] δ 8.45 (d, J=9.0 Hz, 1H), 8.42 (s, 1H), 8.21 (d, J=8.7 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 7.87 (dd, J=8.7, 1.7H, 1H), 7.51 (s, 2H), 4.65-4.57 (m, 1H), 4.57-4.50 (m, 1H), 4.44 (d, J=10.8 Hz, 1H), 4.18 (dd, J=11.3, 3.1 Hz, 1H), 4.05 (dd, J=11.3, 5.9 Hz, 1H). Anal. (C15H12ClF3N2O3S.½H2O) C, H, N.

Workup

  1. extractionthe mixture was extracted with EtOAc (×3)
  2. washThe combined extracts were washed with brine (×3)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b43bf0f27bfc4bf89ae996d421661b17
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…