Hydrochloric Acid → Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

HRID 344834노트

반응식

HRID 344834 반응식
CON(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li]CCCC.Cl>O1CCCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH2:7])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

생성물 1

HCID 10935571Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of N-methoxy-N-methyl anthranilic acid amide prepared as in Example 1(A)(2.00 g, 11.1 mmol) and 4-benzyloxy-bromobenzene (2.92 g, 11.1 mmol) in anhydrous tetrahydrofuran (65 ml) at -78° C. under nitrogen is added, with vigorous stirring, n-BuLi in hexanes (13.8 ml, 1.6M, 22.2 mmol) at 0.60 ml/min. After 20 min, aqueous hydrochloric acid is added (1N, 20 ml), the mixture extracted with ethyl acetate (150 ml), ethyl acetate washed with water, brine, dried over magnesium sulfate, and concentrated. Recrystallization from hexanes gave 4'-benzyloxy-2-aminobenzophenone as yellow crystals; yield: 2.35 g, (70%); m.p. 99°-101° C.

후처리

  1. customat -78° C.
  2. extractionthe mixture extracted with ethyl acetate (150 ml), ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from hexanes

출처 및 근거

ORD 기록
ord-117daf84d97946babe1347d2abf4bc03
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053543

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