Potassium Carbonate → N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-4-chlorobutanamide

HRID 80532Notes

Reaction equation

HRID 80532 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([NH:13][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][Cl:14])=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 5542155-(4-Bromophenyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 3475484N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-4-chlorobutanamideYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-(4-bromophenyl)-1,3,4-thiadiazol-2-amine (10.2 g, 0.04 mol), 4-chlorobutyryl chloride (11.3 g, 9.0 ml, 0.08 mol) and potassium carbonate (5.5 g, 0.04 mole) in toluene (100 ml) was heated under reflux for 4 hr. The toluene was then evaporated under reduced pressure. The residue was then quenched with water, stirred, and filtered. The solid obtained was washed, dried and recrystallized from toluene to give the required product (12.5 g, 87% yield), mp 187-9° C., m/e 360, 15.7% (consistent with molecular formula C12H11BrClN3OS, calcd. 360.66). 1H NMR (DMSO-d6): δ 1.96-2.22 (m, 2H, —CH2), 2.69-2.81 (m, 2H, —CH2), 3.71-3.72 (m, 2H, —CH2), 7.49-7.88 (dd, 4H, ArH), 12.76 (br s, 1H, NH). 13C NMR: δ 27.3, 32.1, 44.6, 123.8, 128.7, 129.4, 132.3, 158.5, 160.7, 170.7.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. customThe toluene was then evaporated under reduced pressure
  4. customThe residue was then quenched with water
  5. filtrationfiltered
  6. customThe solid obtained
  7. washwas washed
  8. customdried
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-9da5ff71e88645ccaa44b1c3a0cae9bf
Source dataset
uspto-grants-2014_09
Patent number
US08846665B2

Reaction notes

Loading…