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 2076142Notes

Reaction equation

HRID 2076142 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-32ce4e6f5b844d669585f0e0188f4f2b
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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