Water → HCID 86604152, compound

HRID 1867248Notes

Reaction equation

HRID 1867248 reaction equation
Cl.Cl.CNN(NC)C(N)=[N:7][S:8][CH2:9][CH2:10][CH3:11].C[CH2:16][N:17]([CH:21](C)C)[CH:18](C)C.C1C(C[Cl-]C([O-])=O)=CC=C([N+:35]([O-])=O)C=1.O>C(Cl)Cl>[CH3:21][N:17]([CH3:16])[C:18]([NH2:35])=[N:7][S:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 86604153HCID 86604153, compoundHCID 178525823HCID 178525823, compound

Product 1

HCID 86604152HCID 86604152, compoundYield 126.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N,N-Dimethylaminopropyl thioguanidine dihydrochloride (1.71 mmol, 400 mg) was suspended in dry DCM and cooled to 0° C. under N2 atm. DIEA (6.0 mmol, 775 mg) was then added over 5 min. and the mixture stirred until it became homogeneous (5-10 min). A solution of 4-nitrobenzylchloroformate (2.05 mmol, 445 mg) in dry DCM (10 mL) was then added via syringe over 15 minutes and the resulting mixture was allowed to warm to rt overnight. The crude reaction mixture was then washed with DI water and 50% brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the resulting residue by column chromatography on silica get with 9:1 ACN:DI water afforded the desired product (106, 350 mg, 40% yield) as a white foamy solid.

Workup

  1. custom(5-10 min)
  2. temperatureto warm to rt overnight
  3. customThe crude reaction mixture
  4. washwas then washed with DI water and 50% brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the resulting residue by column chromatography on silica
  9. customget with 9:1 ACN

Sources & evidence

ORD record
ord-5fa152d183084ae69ebb44e58f34ffe9
Source dataset
uspto-grants-2009_12
Patent number
US07632828B2

Reaction notes

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