Thiourea → HCID 57900505, compound

HRID 84568Notes

Reaction equation

HRID 84568 reaction equation
Br[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[C:3]([C:5]1[S:18][C:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[O:11][CH2:12][CH2:13][C:7]=2[CH:6]=1)=O.[NH2:26][C:27]([NH2:29])=[S:28]>CC(C)=O>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:2]1[S:28][C:27]([NH2:29])=[N:26][C:3]=1[C:5]1[S:18][C:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[O:11][CH2:12][CH2:13][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 57900192HCID 57900192, compound

Product 1

HCID 57900505HCID 57900505, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of crude 2-bromo-2-(2-chlorophenyl)-1-(4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)ethanone (0.21 mmol) in 2 mL acetone was treated with thiourea (48 mg) and the resultant suspension was heated at 80° C. overnight. The reaction mixture was cooled to room temperature and concentrated. The crude residue was purified by reverse phase HPLC to give 280 as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ 7.65 (m, 1H), 7.55-7.53 (m, 2H), 7.47-7.43 (m, 2H), 7.29 (br s, 2H), 7.14 (m, 1H), 7.02 (m, 1H), 6.45 (s, 1H), 4.17 (t, 2H), 2.95 (t, 2H). MS: (ESI+) 411.1

Workup

  1. concentrationconcentrated
  2. customThe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-652928ae38b642bcb1819adbf8f0f692
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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