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

HRID 80532ノート

反応式

HRID 80532 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9da5ff71e88645ccaa44b1c3a0cae9bf
出典データセット
uspto-grants-2014_09
特許番号
US08846665B2

反応ノート

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