Methyl isothiocyanate → 4-Methyl-2-(methylamino)-1,3-benzothiazole-5-carboxylic acid

HRID 1263411ノート

反応式

HRID 1263411 の反応式
[NH2:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][N:13]=[C:14]=[S:15].BrBr>C(O)(=O)C>[CH3:12][NH:13][C:14]1[S:15][C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH3:11])[C:2]=2[N:1]=1

参加物

5

反応物 3

HCID 11167Methyl isothiocyanateHCID 24408BromineHCID 27336993-Amino-2-methylbenzoic acid

生成物 1

HCID 186160494-Methyl-2-(methylamino)-1,3-benzothiazole-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒3 回

反応条件

温度
100 °C

実験手順

99 g of 3-amino-2-methylbenzoic acid (0.655 mol) were initially charged in 500 ml of acetic acid and, at 80° C,. admixed with 51 g of methyl isothiocyanate (7 mol) in 100 ml of acetic acid. After 2 h, 106 g of bromine (0.66 mol) in 20 ml of acetic acid were added dropwise at 50° C. The mixture was subsequently heated at about 100° C. for 2 h and, after the reaction had ended, allowed to cool. The precipitate was filtered off, the filtrate was concentrated to about 50 ml and the remaining filtrate and the precipitate were added to water. The aqueous phase was adjusted to pH 5 and the precipitate was filtered off at 8° C. It was subsequently washed with water and dried. Yield: 66 g (42%).

後処理

  1. temperatureto cool
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated to about 50 ml
  4. additionthe remaining filtrate and the precipitate were added to water
  5. filtrationthe precipitate was filtered off at 8° C
  6. washIt was subsequently washed with water
  7. customdried

出典と根拠

ORDレコード
ord-01832ae01f6b43ccbfa4faece788c228
出典データセット
uspto-grants-2003_04
特許番号
US06541423B1

反応ノート

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