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

HRID 80532노트

반응식

HRID 80532 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9da5ff71e88645ccaa44b1c3a0cae9bf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846665B2

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