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

HRID 1263411노트

반응식

HRID 1263411 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-01832ae01f6b43ccbfa4faece788c228
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541423B1

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