Benzene → HCID 21832193, compound

HRID 1682731Notes

Reaction equation

HRID 1682731 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[OH:4].O=[C:16]([CH3:33])[CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[F:14][C:11]([F:12])([F:13])[C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][CH:16]([CH3:33])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:31][CH:32]=2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 305142-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 21832193HCID 21832193, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 2, but using 5.88 g of 2-amino-1-(3-trifluoromethylphenyl)ethanol (prepared as described in Preparation 42), 8 g of 5-[4-(2-oxopropoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Preparation 2), 200 ml of benzene, 150 ml of absolute methanol and 5.4 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 4.8 g of the title compound were obtained as crystals, melting at 100°-105° C.

Workup

  1. custompurifying the reaction product by column chromatography through silica gel

Sources & evidence

ORD record
ord-875c350b694843c4947830139564d43b
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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