Triethylamine → HCID 15617527, compound

HRID 2165498Notes

Reaction equation

HRID 2165498 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([SH:25])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>CN(C)C=O.C1(C)C=CC=CC=1>[F:27][C:18]([F:17])([F:26])[C:19]1[CH:20]=[C:21]([S:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH:11]=[O:12])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1367513-(Trifluoromethyl)benzenethiolHCID 15617526HCID 15617526, compound

Product 1

HCID 15617527HCID 15617527, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To N,N-dimethylformamide (30 ml) and 2-(7-bromoheptyl) benzaldehyde (1.5 g, 5 mmoles) was added a solution of 3-trifluoromethylthiophenol (1.0 ml, 8 mmoles) and triethylamine (3.0 ml, 0.02 mole) in N,N-dimethylformamide (20 ml). The reaction mixture was heated to (35 90° C. for 1 hour and then stirred for 11/2 hours while slowly cooling to room temperature. The mixture was diluted with toluene and evaporated, followed by dilution with methylene chloride. The solution was evaporated and flash chromatographed using 8% ethyl acetate in hexane to give the desired product.

Workup

  1. temperaturewhile slowly cooling to room temperature
  2. customevaporated
  3. customThe solution was evaporated
  4. customflash chromatographed

Sources & evidence

ORD record
ord-acf9f8bfbeb949e693b09c7eae302656
Source dataset
uspto-grants-1990_07
Patent number
US04939279

Reaction notes

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