Diisopropylethylamine → HCID 178513103, compound

HRID 2224069Notes

Reaction equation

HRID 2224069 reaction equation
[C:1]1([S:7]([C:10]2[CH:22]=[CH:21][C:13]3[N:14]([C:18](Cl)=[O:19])[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29].C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]1([S:7]([C:10]2[CH:22]=[CH:21][C:13]3[N:14]([C:18]([NH:29][C:28]([NH2:30])=[NH:27])=[O:19])[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 286947Carbonic acid-guanidine (1:1)HCID 586415087-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl chloride

Product 1

HCID 178513103HCID 178513103, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl chloride (0.360 g., 1 mmol) in 20 mL acetonitrile, was added guanidine carbonate (0.180 g., 1 mmol), followed by the dropwise addition of N,N-diisopropyl ethylamine (0.523 mL, 3 mmol.) The reaction mixture was partitioned between 50 mL each of water and ethyl acetate. The organic fraction was washed with dilute aqueous hydrogen chloride followed by 50 mL water. The organic fraction was dried over sodium sulfate and concentrated in vacuo. The resulting white solid was dissolved in 20 mL refluxing dichloromethane. On cooling, white crystals formed, which were filtered and dried under vacuum to give 73 mg (21 %) of N-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-guanidine free base, which recrystallized from EtOH/HCl/Et2O to provide the hydrochloride salt. MS: 361 (M+H)+, mp (as hydrochloride): 148.5-151.6° C.

Workup

  1. customwas partitioned between 50 mL each of water and ethyl acetate
  2. washThe organic fraction was washed with dilute aqueous hydrogen chloride
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting white solid was dissolved in 20 mL
  6. temperaturerefluxing dichloromethane
  7. temperatureOn cooling
  8. customwhite crystals formed
  9. filtrationwhich were filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-0010377bef2c49f5bb6948233472bc7c
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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