Hydrochloric Acid → HCID 57637329, compound

HRID 2111232Notes

Reaction equation

HRID 2111232 reaction equation
C(=NN[C:16]1[CH:17]=[C:18]([CH2:37][N:38]([CH3:40])[CH3:39])[S:19][C:20]=1[CH:21]=[N:22][N:23]=C(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:40][N:38]([CH3:39])[CH2:37][C:18]1[S:19][C:20]2[CH:21]=[N:22][NH:23][C:16]=2[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 76571858HCID 76571858, compound2×

Product 1

HCID 57637329HCID 57637329, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To [4-(N′-Benzhydrylidene-hydrazino)-5-(benzhydrylidene-hydrazonomethyl)-thiophen-2-ylmethyl]-dimethyl-amine [Intermediate (4)] in ethanol (100 mL) was added 50 mL of concentrated hydrochloric acid. The dark red mixture is stirred at 85° C. for 2 hours. Water is added followed by solid sodium carbonate until pH is slightly basic. The reaction mixture is then extracted twice with ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated. The residue is chromatographed (ethyl acetate—1.0M ammonia in methanol, 90:10 as eluant) to produce dimethyl-(1H-thieno[3,2-c]pyrazol-5-ylmethyl)-amine [1.06 g, 45% Intermediate (5)] as a brown solid. LC/MS: RT=0.4 minutes, 182.09 m/e (M+H).

Workup

  1. extractionThe reaction mixture is then extracted twice with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed (ethyl acetate—1.0M ammonia in methanol, 90:10 as eluant)

Sources & evidence

ORD record
ord-60f2642e9ca24995bd99fa6bde388a60
Source dataset
uspto-grants-2009_04
Patent number
US07518000B2

Reaction notes

Loading…