Trichloromethanethiol → 3-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole

HRID 1436443노트

반응식

HRID 1436443 반응식
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[NH:11])[NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:19][C:20]([SH:23])(Cl)Cl>C(Cl)Cl>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:20]([Cl:19])[S:23][N:11]=2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6390TrichloromethanethiolHCID 8471TriethylamineHCID 122077144-Bromobenzene-1-carboximidamide--hydrogen chloride (1/1)

생성물 1

HCID 118326413-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole수율 28%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

4-Bromobenzenecarboximidamide hydrochloride (1.00 g, 4.25 mmol), prepared in the previous step, was suspended in methylene chloride (25 mL) and triethylamine (6.1 mL, 42.5 mmol) was added and the mixture was cooled to 0° C. Perchloromethyl mercaptan (0.47 g, 4.25 mmol) was added slowly, the mixture was stirred for 30 min, warmed to 25° C. and stirred 4 h. The mixture was diluted with methylene chloride, filtered through the Celite™ reagent, and concentrated. Flash chromatography (2% acetone in hexane) afforded 3-(4-bromophenyl)-5-chloro-1,2,4-thiadiazole (327 mg, 28%). HRMS: calcd for C8H4BrClN2S, 273.89671; found (EI, M+.), 273.8968; Analytical HPLC: purity 100% at 210-370 nm, 11.2 min; 100% at 272 nm, 11.2 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

후처리

  1. temperaturewarmed to 25° C.
  2. stirringstirred 4 h
  3. filtrationfiltered through the Celite™ reagent
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-67a846e3c7184bf68bc721306029be22
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618990B2

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