Sodium Hydroxide → 2-(hydroxymethyl)-4-methoxy-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenol

HRID 1691500

반응식

HRID 1691500 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[N+:23]([O-])=O)[C:4]=1[OH:26].[OH-].[Na+].C(S(O)=O)(N)=N>O.C(O)CC>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([N:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]3=[N:23]2)[C:4]=1[OH:26]

참가 물질

6

반응물 3

HCID 14798Sodium Hydroxide2회HCID 61274Thiourea dioxideHCID 1361233912-(Hydroxymethyl)-4-methoxy-6-((2-nitro-4-(trifluoro-methyl)-phenyl)diazenyl)-phenol

생성물 1

HCID 593174032-(hydroxymethyl)-4-methoxy-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenol수율 31.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 10311-Propanol용매

반응 조건

온도
80 °C

실험 절차

In a 250 ml round bottom flask equipped with a magnetic stirrer was added 7.70 g (20.7 mmol) 2-(hydroxymethyl)-4-methoxy-6-((2-nitro-4-(trifluoromethyl)phenyl)diazenyl)-phenol from Example 2 part 1, 25 ml deionized water, 1.85 g sodium hydroxide, and 80 ml 1-propanol. The mixture was heated to 80° C. and 6.55 g (60.6 mmol) formamidine sulfinic acid (Aldrich) was added slowly and concurrently with a solution of 3.0 g NaOH in 50 ml deionized water. The reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was cooled at −20° C. for 2 hours and filtered. The solid was dissolved in 2.5 L deionized water containing 4 grams NaOH. The pH was adjusted to 2.0 using 1 N HCl. The resultant solid was filtered, washed with ample amounts of deionized water, filtered and dried to give 2.2 g (31%) of a yellow solid. 1H NMR (CDCl3) delta: 11.03 (s, 1H, Ar—OH), 8.30 (s, 1H, Ar—H benzotriazole 4-position), 8.07 (d, 1H, Ar—H benzotriazole 6-position), 7.88 (s, 1H, Ar—H phenol), 7.69 (d, 1H, Ar—H benzotriazole), 7.08 (s, 1H, Ar—H phenol), 4.84 (s, 2H, Ar—CH2), 3.90 (s, 3H, Ar—OCH3).

후처리

  1. customIn a 250 ml round bottom flask equipped with a magnetic stirrer
  2. temperatureThe reaction mixture was heated at 80° C. for 2 hours
  3. temperatureThe reaction mixture was cooled at −20° C. for 2 hours
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in 2.5 L
  6. filtrationThe resultant solid was filtered
  7. washwashed with ample amounts of deionized water
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-e598a5e42e7d4603aa652a89da02770b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153703B2

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