Hydrochloric Acid → 6,7-Difluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131383

반응식

HRID 131383 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10]2[S:11][C:12]([CH3:17])=[CH:13][C:14]=2[C:15]#[N:16])=[C:4]([N+:18]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)[Cl:24].Cl>C(O)C>[ClH:24].[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]2[N:18]=[C:15]([NH2:16])[C:14]3[CH:13]=[C:12]([CH3:17])[S:11][C:10]=3[NH:9][C:5]=2[CH:6]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 586260262-(4,5-Difluoro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

생성물 1

HCID 1363885776,7-Difluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride수율 100%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
86.5 °C

실험 절차

Add 2-(4,5-difluoro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile (94.0 g, 318 mmol) and tin (II) chloride dihydrate (225 g, 997 mmol) to ethanol (1400 mL) and aqueous 6N HCl (1400 mL) with stirring under nitrogen. Heat at gentle reflux (86-87° C.) for 0.3 hours, and then allow cooling to ambient temperature. Filter, rinse with water (3×250 mL) and dry at 50-60° C. to give 95.7 g (100%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.41 (bs, 1H), 9.84 (bs, 1H), 9.33 (bs, 1H), 8.93 (bs, 1H), 7.00 (m, 2H), 6.85 (s, 1H), 2.28 (s, 3H). HRMS (ES) exact mass M+H calcd for C12H9F2N3S (freebase) 266.0563; found 266.0555.

후처리

  1. temperatureHeat
  2. temperatureallow cooling to ambient temperature
  3. filtrationFilter
  4. washrinse with water (3×250 mL)
  5. customdry at 50-60° C.

출처 및 근거

ORD 기록
ord-864a9ab7a1f9408f9ff352b9bb18353c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

연결된 노트

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