Hydrochloric Acid → HCID 24071726, compound

HRID 1747316Notes

Reaction equation

HRID 1747316 reaction equation
C([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:5]1=[O:24])(C)=C.O.Cl.C(Cl)Cl>CO>[C:14]1([CH2:13][N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:4][C:5]2=[O:24])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 6344DichloromethaneHCID 59497686HCID 59497686, compound

Product 1

HCID 24071726HCID 24071726, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-Isopropenyl-3-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one (1.6 g, 5.1 mmol) is dissolved in MeOH (5.0 mL) and water (5.0 mL) is added into the solution. To this heterogeneous reaction mixture is added 37% hydrochloric acid (4.0 mL). The reaction mixture is heated to 60° C. for 30 min and then water (50 mL) and CH2Cl2 (50 mL) are added. The organic layer is separated and the aqueous layer is extracted with CH2Cl2 (3×50 mL). The organic layers are combined, washed with Sat. NaHCO3 (100 mL), Sat. NH4Cl (100 mL) and water (3×100 mL), dried over MgSO4 and concentrated to give 1.3 g (93%) of crude product which is pure enough for the next step.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with CH2Cl2 (3×50 mL)
  3. washwashed with Sat. NaHCO3 (100 mL), Sat. NH4Cl (100 mL) and water (3×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fdd2c17ffa0748c18ad81812542b1378
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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