Dichloromethane → HCID 10577722, compound

HRID 1451820Notes

Reaction equation

HRID 1451820 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1[C:30]2[C:25](=[CH:26]C=C[CH:29]=2)[CH:24]=[CH:23][C:22]=1[S:31]([CH:34]1[S:38][C:37](=[O:39])[NH:36][C:35]1=[O:40])(=[O:33])=[O:32].C(N(CC)CC)C.ClCCl>O>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:36]2[C:35](=[O:40])[CH:34]([S:31]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:30][CH:29]=3)(=[O:32])=[O:33])[S:38][C:37]2=[O:39])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 108286095-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione

Product 1

HCID 10577722HCID 10577722, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylmethyl chloride (2.67 g, 9.58 mmol) was added to a stirred, room temperature solution of 5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [(V), from Example 12, 1.30 g, 4.79 mmol], triethylamine (0.67 mL, 4.79 mmol) and dichloromethane (6.5 mL). After 1 h, water (300 mL) was added and the organic material was extracted with ethyl acetate (2×200 mL). The combined extracts were dried (brine, MgSO4), concentrated and purified by flash chromatography (4:1 petroleum ether:ethyl acetate) to provide the title compound as a white solid (1.1 g, 45%): mp 105°-110° C.; NMR (CDCl3): δ7.85 (d, J=8.3 Hz, 2H, ArH), 7.48 (d, J=8.1 Hz, 6H, CPh3H), 7.38 (d, J=8.3 Hz, 2H, ArH),7.23 (m, 9H, CPh3H), 5.13 (s, 1H, CH), 2.46 (s, 3H, CH3).

Workup

  1. extractionthe organic material was extracted with ethyl acetate (2×200 mL)
  2. dry with materialThe combined extracts were dried (brine, MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (4:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-e4c3d416364940a79b3da91f211de5bb
Source dataset
uspto-grants-1997_02
Patent number
US05605918

Reaction notes

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