N-Iodosuccinimide → HCID 59208476, 화합물

HRID 2243073노트

반응식

HRID 2243073 반응식
IN1C(=O)CCC1=O.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18].[NH2:22][C:23]([NH2:25])=[S:24]>CCOC(C)=O.CO>[NH2:25][C:23]1[S:24][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:11]2[N:10]([CH3:9])[CH:14]=[CH:13][N:12]=2)[N:22]=1

참가 물질

6

반응물 3

HCID 120273N-IodosuccinimideHCID 2723790ThioureaHCID 20029381Methyl 3-(1-Methyl-2-imidazolyl)-3-oxopropionate2회

생성물 1

HCID 59208476HCID 59208476, 화합물수율 46.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

N-Iodosuccinimide (9.3 g, 41 mmol) was added to a mixture of 7.52 g (41 mmol) methyl 3-(1-methyl-1H-imidazol-2-yl)-3-oxopropanoate (Intermediate 63) and 7.5 g Amberlyst-15 resin in 400 ml EtOAc followed by stirring for 1 hour at room temperature. The resin was filtered off and rinsed with EtOAc. Solvent was removed from the filtrate and the residue was taken up in diethyl ether. Insoluble material was filtered off and rinsed with additional ether. Solvent was removed from the filtrate and the residue was dissolved in 200 ml MeOH before addition of 4.7 g (62 mmol) thiourea. The mixture was heated at reflux for 1 hour, then the solvent was removed and the residue was taken up in aqueous Na2CO3. Insoluble material was collected by filtration and rinsed well with water. The solids were dried in vacuo affording 4.51 g of the title compound: MS (ES) (M+H)+: 239 for C9H10N4O2S; NMR: 3.48 (s, 3H), 3.57 (s, 3H), 6.90 (s, 1H), 7.12 (s, 1H), 7.98 (s, 2H).

후처리

  1. filtrationThe resin was filtered off
  2. washrinsed with EtOAc
  3. customSolvent was removed from the filtrate
  4. filtrationInsoluble material was filtered off
  5. washrinsed with additional ether
  6. customSolvent was removed from the filtrate
  7. temperatureThe mixture was heated
  8. temperatureat reflux for 1 hour
  9. customthe solvent was removed
  10. filtrationInsoluble material was collected by filtration
  11. washrinsed well with water
  12. customThe solids were dried in vacuo

출처 및 근거

ORD 기록
ord-bcc0ebdece1c47acac24508df8ba6fe1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674801B2

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