2-Bromo-6-phenylcyclohexanone → [4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076142노트

반응식

HRID 2076142 반응식
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)[S:4][N:3]=1.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=O>C(O)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[S:15][C:26]4[CH2:27][CH2:28][CH2:29][CH:24]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=5)[C:25]=4[N:16]=3)=[CH:11][CH:12]=2)[S:4][N:3]=1

참가 물질

4

반응물 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632617[4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thiourea

생성물 1

HCID 44193963[4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine수율 10%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of [4-(3-methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thiourea (75 mg, 0.3 mmol) and 2-bromo-6-phenyl-cyclohexanone (84 mg, 0.33 mmol) in ethanol (3 ml) was heated to reflux over night. The precipitated solid, unreacted thiourea, was filtered off after cooling to room temperature and washed with ethanol. The filtrate was evaporated under reduced pressure and the residue was purified on silica gel using heptane/ethyl acetate (4:1 v/v) as the eluent to yield the title compound (12 mg, 10%) as a yellow solid. MS ISP (m/e): 405.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.51 (br s, 1H, NH), 7.82 (d, 2H), 7.58 (d, 2H), 7.28 (t, 2H), 7.19 (t, 1H), 7.13 (d, 1H), 4.07 (m, 1H), 2.72 (m, 2H), 2.58 (s, 3H), 2.13 (m, 1H), 1.70-1.90 (m, 3H).

후처리

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid, unreacted thiourea, was filtered off
  3. washwashed with ethanol
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was purified on silica gel

출처 및 근거

ORD 기록
ord-32ce4e6f5b844d669585f0e0188f4f2b
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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