Acetone → 4-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-5-(2-chlorophenyl)thiazol-2-amine

HRID 1949823Notes

Reaction equation

HRID 1949823 reaction equation
Br[CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[C:3]([C:5]1[S:19][C:8]2[C:9]3[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:10]=3[O:11][CH2:12][CH2:13][C:7]=2[CH:6]=1)=O.CC(C)=O.[NH2:31][C:32]([NH2:34])=[S:33]>>[Br:18][C:15]1[CH:16]=[CH:17][C:9]2[C:8]3[S:19][C:5]([C:3]4[N:31]=[C:32]([NH2:34])[S:33][C:2]=4[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:26])=[CH:6][C:7]=3[CH2:13][CH2:12][O:11][C:10]=2[CH:14]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 2723790ThioureaHCID 579003952-Bromo-1-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone

Product 1

HCID 579002274-(8-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-5-(2-chlorophenyl)thiazol-2-amineYield 84.6%

Conditions

Temperature
80 °C

Procedure

2-Bromo-1-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-2-(2-chlorophenyl)ethanone (ca. 2.3 mmol) was suspended in acetone (15 mL, 0.20 mol) and treated with thiourea (0.26 g, 0.0034 mol). The mixture was sealed and heated at 80° C. for 3 h. After cooling to room temperature, the reaction mixture was concentrated, suspended in water and the solid was collected by filtration. The solid was rinsed with water to give 953 mg of 271 as a light yellow solid. 1H NMR (dmso-d6, 500 MHz) δ 7.64 (m, 1H), 7.53 (m, 2H), 7.45 (m, 1H), 7.35 (m, 1H), 7.23 (m, 1H), 7.17 (m, 1H), 6.47 (s, 1H), 4.19 (t, 2H), 2.95 (t, 2H). MS (ESI) 491.0

Workup

  1. customThe mixture was sealed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated
  4. filtrationthe solid was collected by filtration
  5. washThe solid was rinsed with water

Sources & evidence

ORD record
ord-763d2584ab0c48f7aea88924de6e04d7
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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