Hydrochloric Acid → 2-(5-Fluoro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

HRID 131342

반응식

HRID 131342 반응식
[NH2:1][C:2]1[S:3][C:4]([CH3:9])=[CH:5][C:6]=1[C:7]#[N:8].F[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].O.[OH-].[Li+].Cl>O.CS(C)=O>[F:17][C:15]1[CH:14]=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[C:11]([NH:1][C:2]2[S:3][C:4]([CH3:9])=[CH:5][C:6]=2[C:7]#[N:8])[CH:16]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

생성물 1

HCID 586259392-(5-Fluoro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile수율 62%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

Add 2-amino-5-methyl-thiophene-3-carbonitrile (10.0 g, 72.4 mmol) and 2,4-difluoro-1-nitro-benzene (8.00 mL, 73.0 mmol) to DMSO (130 mL) and stir under nitrogen at ambient temperature. Add lithium hydroxide monohydrate (6.10 g, 145 mmol) in one portion and stir at ambient temperature. After 18 hours, add deionized water (390 mL) dropwise at 10-20° C. Adjust the pH to 7-8 with concentrated HCl (˜6 mL) and stir for 4 hours. Filter the crude product and rinse with 3:1/water: DMSO, then water. Dry at 50° C. to constant weight. Purify by flash chromatography, eluting with methylene chloride to give the title compound 10.3 g (62%): 1H NMR (400 MHz, DMSO-d6) δ 9.83 (bs, 1H), 8.28 (m, 1H), 7.12 (s, 1H), 6.91 (m, 1H), 6.73 (m, 1H), 2.53 (s, 3H). HRMS (ES) exact mass M+H calcd for C12H8FN3O2S 300.0219; found 300.0219.

후처리

  1. stirringstir for 4 hours
  2. filtrationFilter the crude product
  3. washrinse with 3:1/water
  4. customDry at 50° C. to constant weight
  5. customPurify by flash chromatography
  6. washeluting with methylene chloride

출처 및 근거

ORD 기록
ord-4acee4ebf9f04702ae3394d9518dbba9
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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