Dichloromethane → 6-(Trifluoromethoxy)-1H-benzo[d]imidazol-2-amine hydrochloride

HRID 728567노트

반응식

HRID 728567 반응식
[C-:1]#[N:2].[Na+].BrBr.[F:6][C:7]([F:18])([F:17])[O:8][C:9]1[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=1.[Cl:19]CCl>O.ClCC(Cl)(Cl)Cl>[ClH:19].[F:6][C:7]([F:17])([F:18])[O:8][C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[C:1]([NH2:2])[NH:16][C:11]=2[CH:10]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 24408BromineHCID 27739594-(Trifluoromethoxy)benzene-1,2-diamine

생성물 1

HCID 147006146-(Trifluoromethoxy)-1H-benzo[d]imidazol-2-amine hydrochloride

시약·촉매·용매 2

HCID 962Water용매3회HCID 124181,1,1,2-Tetrachloroethane용매

실험 절차

Sodium cyanide (1.79 9), dissolved in water (5.6 cc) is added dropwise to a mixture, cooled to 0° C., of bromine (5.8 9) and water (5.6 cc). After 1 hour's contact at 0° C., a solution of 4-trifluoromethoxy-1,2-benzenediamine (7 g) in tetrachloroethane (7 cc) is added dropwise. After 2 hours at 0° C., the reaction mixture is poured into water (500 cc). Dichloromethane (500 cc) is added and the mixture is stirred for 20 minutes. After settling has taken place, the aqueous phase is separated and washed with dichloromethane (2×150 cc) and alkalinized to pH 8 with sodium carbonate. The base is extracted with ethyl acetate (3×300 cc) and the organic phase is dried over magnesium sulphate and evaporated under reduced pressure. Crude base (9.5 g) is obtained, which is purified by preparative HPLC using a dichloromethane/ethanol mixture (95:5 by volume) as eluent. An oil is recovered, which is converted to a hydrochloride in ethyl ether. 5-Trifluoromethoxy-2-benzimidazolamine hydrochloride (4.8 g), m.p. 180° C., is obtained.

후처리

  1. additionis added dropwise to a mixture
  2. waitAfter 2 hours at 0° C.
  3. customthe aqueous phase is separated
  4. washwashed with dichloromethane (2×150 cc)
  5. extractionThe base is extracted with ethyl acetate (3×300 cc)
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customCrude base (9.5 g) is obtained
  9. customwhich is purified by preparative HPLC
  10. customAn oil is recovered

출처 및 근거

ORD 기록
ord-289d7e82b199418c8c0009eb0d208684
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049574

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