2-Amino-5-bromobenzoic acid → HCID 4444271, 화합물

HRID 1108250노트

반응식

HRID 1108250 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:18]=[C:19]=[S:20])[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1>C(O)C>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:19](=[S:20])[N:18]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][O:17]1)[C:4]2=[O:6]

참가 물질

4

반응물 2

HCID 798582-Amino-5-bromobenzoic acidHCID 1421082-(Isothiocyanatomethyl)oxolane

생성물 1

HCID 4444271HCID 4444271, 화합물수율 90.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-5-bromobenzoic acid (8.0 g, 37.0 mmol), tetrahydrofurfuryl isothiocyanate (5.0 g, 34.9 mmol) and triethylarine (5.0 mL, 3.6 g, 35.6 mmol) in ethanol (48 mL) was heated at reflux for 2 h. The reaction mixture was then allowed to cool to room temperature and filtered. The resulting filter cake was washed with 50 mL of cold ethanol, followed by 50 mL of hexanes to provide 10.8 g of the title compound of Step A as a solid melting at 230-232° C. IH NMR (400 MHz, Me2SO-d6): δ 1.63-2.0 (m,4H), 3.58-3.68 (m,1H), 3.74-3.82 (m,1H), 4.32 (dd,1H), 4.39-4.50 (m,1H), 4.58 (dd,1H), 7.37 (d,1H), 7.91 (d,1H), 8.02 (s,1H), 13.1 (br s,1H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. filtrationThe resulting filter cake
  5. washwas washed with 50 mL of cold ethanol

출처 및 근거

ORD 기록
ord-551cd97bcd5146e39f57fa1a6fb09f6e
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066638

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