Thiourea → (7-Bromo-5-methyl-2,3-dihydrobenzo[b]oxepin-4-yl)methyl carbamimidothioate hydrochloride

HRID 1911022Notes

Reaction equation

HRID 1911022 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[O:6][CH2:7][CH2:8][C:9]([CH2:12][Cl:13])=[C:10]([CH3:11])[C:4]=2[CH:3]=1.[NH2:16][C:17]([NH2:19])=[S:18]>C(O)C>[ClH:13].[C:17]([S:18][CH2:12][C:9]1[CH2:8][CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:2]([Br:1])=[CH:3][C:4]=2[C:10]=1[CH3:11])(=[NH:16])[NH2:19]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 866854227-Bromo-4-(chloromethyl)-5-methyl-2,3-dihydrobenzo[b]oxepine

Product 1

HCID 86685423(7-Bromo-5-methyl-2,3-dihydrobenzo[b]oxepin-4-yl)methyl carbamimidothioate hydrochlorideYield 102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-bromo-4-(chloromethyl)-5-methyl-2,3-dihydrobenzo[b]oxepine from step H7 (2.05 g, 7.13 mmol) in ethanol (75 mL) was added thiourea (0.651 g, 8.55 mmol). The mixture was refluxed for 3 h. A white solid precipitated. The solvent was removed. The solid residue was washed with hexanes and dried in vacuo to give a (7-bromo-5-methyl-2,3-dihydrobenzo[b]oxepin-4-yl)methyl carbamimidothioate hydrochloride (2.64 g, 7.26 mmol, 102% yield). The crude mixture was used in the next step without further purification. 1H NMR (500 MHz, methanol-d4) δ 7.48 (d, J=2.4 Hz, 1H), 7.43-7.36 (m, 1H), 6.97 (d, J=8.5 Hz, 1H), 4.53 (t, J=6.3 Hz, 2H), 4.25 (s, 2H), 2.34 (t, J=6.1 Hz, 2H), 2.18 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customA white solid precipitated
  3. customThe solvent was removed
  4. washThe solid residue was washed with hexanes
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e1d3a453be67490db58cf8b300b35619
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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