Triethylamine → HCID 9839980, compound

HRID 2187722Notes

Reaction equation

HRID 2187722 reaction equation
Br[CH:2]1[CH:10]([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[C:3]1=[O:13].[C:14]([NH2:22])(=[S:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)(C)C>[Cl:12][C:7]1[CH:6]=[CH:5][C:4]2[C:3]3([OH:13])[N:22]=[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[S:21][CH:2]3[CH:10]([OH:11])[C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 683563ThiobenzamideHCID 18476627HCID 18476627, compound

Product 1

HCID 9839980HCID 9839980, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

0.6 g (2.3 mmol) of 2-bromo-5-chloro-3-hydroxyindan-1-one and 0.473 g (3.45 mmol) of thiobenzamide were dissolved in 5 ml of isopropanol. 0.478 ml (3.45 mmol) of triethylamine was added, and the mixture was then stirred at room temperature for 12 h and subsequently at 50° C. for 8 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel by initially using n-heptane/ethyl acetate 3/1 and then toluene/acetone 5/1. This gave 6-chloro-2-phenyl-8,8a-dihydroindeno[1,2-d]thiazole-3a,8-diol having a melting point of 151-153° C. (with decomposition).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel by initially using n-heptane/ethyl acetate 3/1

Sources & evidence

ORD record
ord-238fe152b23f4aecb9d8c6b84541fe19
Source dataset
uspto-grants-2002_06
Patent number
US06410577B1

Reaction notes

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