Thiourea → 2-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one

HRID 1942996Notes

Reaction equation

HRID 1942996 reaction equation
Br[CH:2]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:11][C:12]([NH2:14])=[S:13]>CCO>[NH2:14][C:12]1[S:13][C:2]2[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[N:11]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 597380522-Bromocycloheptane-1,3-dione

Product 1

HCID 251308282-amino-4H,5H,6H,7H,8H-cyclohepta[d][1,3]thiazol-8-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-bromocycloheptane-1,3-dione (45.17 mmol) in abs. EtOH (100 mL) was added thiourea (3.61 g, 47.43 mmol). The reaction mixture was stirred at room temperature overnight at which point the EtOH was removed under reduced pressure and the resulting dark orange residue was triturated with DCM. The residue was recrystallized from EtOH to afford 26z as an off white solid (6 g, 50% overall crude yield from cycloheptane-1,3-dione). 1H NMR (300 MHz, DMSO-d6): δ 8.87 (br s, 2H), 2.87 (t, J=6 Hz, 2H), 2.64 (t, J=6 Hz, 2H), 1.89-1.85 (m, 2H), 1.81-1.77 (m, 2H);

Workup

  1. customwas removed under reduced pressure
  2. customthe resulting dark orange residue was triturated with DCM
  3. customThe residue was recrystallized from EtOH

Sources & evidence

ORD record
ord-e44376b3615147d7b06d420c1d947507
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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