Methylamine → 1,2,3-Thiadiazole-4-carboxamide, N-methyl-5-(phenylamino)-

HRID 1182213ノート

反応式

HRID 1182213 の反応式
[NH2:1][CH3:2].[Li]CCCC.C(O[C:11]([C:13]1[N:14]=[N:15][S:16][C:17]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:12])C.[NH4+].[Cl-]>C1CCCCC1.CCOC(C)=O>[CH3:2][NH:1][C:11]([C:13]1[N:14]=[N:15][S:16][C:17]=1[NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:12]

参加物

7

反応物 4

HCID 6329MethylamineHCID 25517Ammonium ChlorideHCID 1499213HCID 1499213、化合物HCID 178418339Butyllithium

生成物 1

HCID 14992791,2,3-Thiadiazole-4-carboxamide, N-methyl-5-(phenylamino)-

試薬・触媒・溶媒 2

HCID 8078Cyclohexane溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-30 °C

実験手順

To a solution of 2 M NH2CH3 in cyclohexane (2 mL) at −40° C. was added 0.8 mL of 2 M n-BuLi in cyclohexane under argon. A white precipitate was immediately observed. The mixture was stirred at −30° C. for 0.5 hours, and 5-phenylamino-[1,2,3]thiadiazole-4-carboxylic acid ethyl ester (60 mg, 0.24 mmole) in 1 mL of cyclohexane was slowly added. Greenish solution was immediately obtained. The reaction was slowly warmed up to room temperature and TLC showed a total disappearance of the starting material. A mixture of 7 mL of saturated NH4Cl solution and 7 mL of EtOAc was added to the ice-cooled flask and the solution was stirred for 30 minutes. The aqueous layer was neutralized to pH ˜7 and then extracted with EtOAc. The organic layer was absorbed with silica gel, loaded to a 53 g silica gel column, and eluted with hexane:EtOAc=5:1. A 25 mg white powder was obtained (45%). 1H NMR (ppm, DMSO-d6): 11.00 (br. s, 1H), 8.92 (br. q, 1H), 7.46 (t, 2H), 7.34 (d, 2H), 7.20 (t, 1H), 2.85 (d, 3H).

後処理

  1. customGreenish solution was immediately obtained
  2. temperatureThe reaction was slowly warmed up to room temperature
  3. temperaturecooled flask
  4. stirringthe solution was stirred for 30 minutes
  5. extractionextracted with EtOAc
  6. customThe organic layer was absorbed with silica gel
  7. washeluted with hexane

出典と根拠

ORDレコード
ord-8c3c08c970a94fdc85a592a8898b4243
出典データセット
uspto-grants-2007_10
特許番号
US07288556B2

反応ノート

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