1-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2-bromoethan-1-one → HCID 68704696, compound

HRID 62011Notes

Reaction equation

HRID 62011 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9](=[S:11])[NH2:10])=[CH:7][CH:6]=[CH:5][N:4]=1.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([C:39](=O)[CH2:40]Br)[CH:25]=[C:26]([N+:36]([O-:38])=[O:37])[C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([C:39]2[N:10]=[C:9]([C:8]3[C:3]([C:2]([F:1])([F:12])[F:13])=[N:4][CH:5]=[CH:6][CH:7]=3)[S:11][CH:40]=2)[CH:25]=[C:26]([N+:36]([O-:38])=[O:37])[C:27]=1[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 714457901-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2-bromoethan-1-oneHCID 826719002-(Trifluoromethyl)-3-pyridinecarbothioamide

Product 1

HCID 68704696HCID 68704696, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(trifluoromethyl)pyridine-3-carbothioamide (0.227 g, 1.10 mmol) and 1-[3,4-bis(benzyloxy)-5-nitrophenyl]-2-bromoethanone (0.50 g, 1.10 mmol) were refluxed overnight in absolute ethanol (5 mL). After cooling to room temperature, the reaction mixture was poured onto water (50 mL). The resulting precipitate was filtered off, washed with water (25 mL) and dried. Recrystallisation from dichloromethane/isopropanol afforded 4-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)thiazole, 0.539 g (87%).

Workup

  1. additionthe reaction mixture was poured onto water (50 mL)
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water (25 mL)
  4. customdried
  5. customRecrystallisation from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-6365eebc110043db9bb3f4a65d5db8ff
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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