Hydrochloric Acid → HCID 59497706, compound

HRID 1747280Notes

Reaction equation

HRID 1747280 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[S:6][CH:7]=[C:8]([CH2:9][N:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[N:12](C(C)=C)[C:11]3=[O:22])[C:4]=2[CH:3]=1.CO.O.Cl>C(Cl)Cl.C(Cl)Cl.CO>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[S:6][CH:7]=[C:8]([CH2:9][N:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[NH:12][C:11]3=[O:22])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 59497645HCID 59497645, compound

Product 1

HCID 59497706HCID 59497706, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (0.53 g, 1.56 mmol) was treated with MeOH (5 mL) followed by water (5 mL). To this heterogeneous reaction mixture was added 37% hydrochloric acid (4 mL). This heterogeneous reaction mixture was heated to 80° C. for 30 min. A white solid was precipitated out. TLC indicated that reaction was complete (starting material Rf 0.8, product Rf 0.4, CH2Cl2:MeOH 95:5). The reaction mixture was diluted with CH2Cl2 (at this point a white precipitate was completely soluble in CH2Cl2) and washed with water. The organic phase was dried over Na2SO4 and concentrated to afford 0.44 g (89%) of the desired product as a white solid. This product was used for the next reaction without further purification. LCMS (ESMS): m/z 315.79 (M+H+).

Workup

  1. customA white solid was precipitated out
  2. customTLC indicated that reaction
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1158c65f33048819d5bbcc5c16ed633
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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