2-Amino-4-methylbenzothiazole → 4-Methylbenzo[d]thiazol-2-ol

HRID 469314

반응식

HRID 469314 반응식
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.N([O-])=[O:13].[Na+]>C(O)=O.C(O)(=O)C.Cl.O>[CH3:11][C:7]1[C:5]2[NH:6][C:2](=[O:13])[S:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

참가 물질

7

반응물 2

HCID 151322-Amino-4-methylbenzothiazoleHCID 23668193Sodium Nitrite

생성물 1

HCID 127708804-Methylbenzo[d]thiazol-2-ol

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 284Formic Acid용매HCID 313Hydrochloric Acid용매HCID 962Water용매2회

실험 절차

5.00 g (30.5 mmol) 2-amino-4-methylbenzothiazole in 15.0 mL formic acid, 6.10 mL glacial acetic acid and 112 mL conc. hydrochloric acid were cooled to −5° C. with stirring and slowly combined with a solution of 2.10 g (30.5 mmol) sodium nitrite in 5.0 mL water. The reaction mixture was stirred for 20 min at this temperature, then heated to RT and then refluxed overnight. The cooled mixture was then mixed with water and extracted several times with EtOAc. The combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulphate, filtered and the filtrate was evaporated down.

후처리

  1. stirringThe reaction mixture was stirred for 20 min at this temperature
  2. temperaturerefluxed overnight
  3. extractionextracted several times with EtOAc
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. customdried on sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate was evaporated down

출처 및 근거

ORD 기록
ord-d83cbdc43ff5451f910282499503eb4e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629137B2

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