Hydrochloric Acid → Methyl 3-hydroxy-4-(methylthio)benzoate

HRID 1383530노트

반응식

HRID 1383530 반응식
Cl.N[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[S:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7].N([O-])=[O:16].[Na+]>O>[OH:16][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[S:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21187837Methyl 3-amino-4-(methylthio)benzoateHCID 23668193Sodium Nitrite

생성물 1

HCID 21187893Methyl 3-hydroxy-4-(methylthio)benzoate

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

A stirred solution of concentrated hydrochloric acid (3.2 mL) in water (3.6 mL) at from 0° C. to 5° C. is treated with methyl 3-amino-4-(methylthio)benzoate (1.97 g; that is prepared as described in Reference Example 52), followed by a solution of sodium nitrite (0.82 g) in water (2 mL), at such a rate that the temperature remains from 0° C. to 5° C. The mixture is then allowed to warm to room temperature and it is stirred for a further period of 1 hour. The reaction mixture is treated with water (30 mL) and then heated to 55-60° C., until the evolution of nitrogen ceased (4 hours). The mixture is extracted with dichloromethane (2×100 mL) and the combined organic extracts are dried and concentrated. The resulting brown oil is subjected to flash chroma-tography, eluting with a mixture of diethyl ether and pentane (1:4 v/v), to give methyl 3-hydroxy-4-(methylthio)benzoate (0.6 g) in the form of a yellow solid.

후처리

  1. customthat is prepared
  2. customremains from 0° C. to 5° C
  3. temperatureheated to 55-60° C., until the evolution of nitrogen
  4. custom(4 hours)
  5. extractionThe mixture is extracted with dichloromethane (2×100 mL)
  6. customthe combined organic extracts are dried
  7. concentrationconcentrated
  8. washeluting with a mixture of diethyl ether and pentane (1:4 v/v)

출처 및 근거

ORD 기록
ord-d29ed8a2cda747e093fb986e2fb5c588
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255326B1

반응 노트

불러오는 중…