Water → HCID 66553164, compound

HRID 80533Notes

Reaction equation

HRID 80533 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)=[N:10][N:9]=2)=[CH:4][CH:3]=1.N1CCCCC1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3=[N:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 3475484N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-4-chlorobutanamide

Product 1

HCID 66553164HCID 66553164, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-4-chlorobutan-amide (1.44 g, 0.004 mol) and piperidine (0.7 g, 0.8 ml, 0.008 mol) in toluene (50 ml) was heated under reflux for 3 h. The reaction mixture was cooled, poured into water and stirred. Toluene was separated dried and evaporated to give a crude product which was purified by repeated silica gel and neutral alumina column chromatography eluting with EtOAc/hexane (50:50 v/v) and CHCl3/hexane (80:20 v/v); mp 204-7° C., m/e 324, 78% (consistent with molecular formula C12H10BrN3OS, calcd. 324.20) 1H NMR CDCl3): δ 2.32-2.40 (m, 2H, —CH2), 2.76 (t, J=7.5 Hz, 2H, —CH2), 4.29 (t, J=7.5 Hz, 2H, —CH2), 7.62-7.84 (dd, J=8.5 Hz, 4H, ArH). 13C NMR: δ 18.3, 31.2, 47.9, 125.0, 128.7, 129.5, 132.3, 157.5, 162.9, 173.7.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe reaction mixture was cooled
  4. customToluene was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ca2f1d55acec4862a35a3f0619acc779
Source dataset
uspto-grants-2014_09
Patent number
US08846665B2

Reaction notes

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