2-Bromo-2'-chloroacetophenone → [4-(2-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604884Notes

Reaction equation

HRID 604884 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=O)[CH2:5]Br.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]([NH2:29])=[S:28])[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1>C(Cl)Cl.C(OCC)C.C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]1[N:29]=[C:27]([NH:26][C:16]2[CH:17]=[CH:18][C:19]([N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]3)=[C:14]([O:13][CH3:12])[CH:15]=2)[S:28][CH:5]=1

Participants

4

Reactant 2

HCID 27357852-Bromo-2'-chloroacetophenoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86624682[4-(2-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 100%

Reagents, catalysts & solvents 1

HCID 18956944Methylene chloride diethyl ether ethanolSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from 77 mg (0.33 mmol) 2-chlorophenacylbromide and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The solvent was evaporated under reduced pressure and the crude reaction was stirred with methylene chloride/diethyl ether/ethanol for 15 minutes at room temperature. The product was filtered off and dried to yield 118 mg (100%) [4-(2-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light yellow solid. MS ISP (m/e): 397.1/399.2 (100/44) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.71 (s, 1H), 9.27 (s, 1H), 7.98 (s, 1H), 7.93 (d, 1H), 7.67 (s, 1H), 7.56 (d, 1H), 7.51-7.38 (m, 4H), 7.27 (d, 1H), 3.88 (s, 3H), 2.34 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude reaction
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-95cbfe8455cc488c82bc12967fd6e592
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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