Hydrochloric Acid → HCID 25003272, compound

HRID 1011587Notes

Reaction equation

HRID 1011587 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].[CH3:20][O:21]C(Cl)Cl.Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[C:8]([CH:20]=[O:21])[C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 25006074HCID 25006074, compound

Product 1

HCID 25003272HCID 25003272, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

1.0M Titanium tetrachloride in dichloromethane solution (2 mL, 2.0 mmol) was added to a suspension of 2-aminocarbonylamino-5-(3-chlorophenyl)pyrrole-3-carboxamide (Compound No. 1-25, 140 mg, 0.50 mmol) in dichloromethane (3 mL) at −30° C. and the mixture was stirred for 40 minutes. Moreover, dichloromethyl methyl ether (0.27 mL, 3.0 mmol) was added thereto and the whole was stirred overnight at 4° C. Under ice-cooling, 1N hydrochloric acid (4 mL) was added thereto and the mixture was stirred for 1 hour, and then water (10 mL) was add thereto. The precipitated solid was filtered off, washed with chloroform (10 mL) and water (10 mL), and dried under reduced pressure to give the target compound (120 mg) as a brown solid (Yield 77%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with chloroform (10 mL) and water (10 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3ff38c842c8342218af6d7100fb8de1e
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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