Hydrochloric Acid → benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate

HRID 1585481

Reaction equation

HRID 1585481 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl>C(Cl)Cl.O>[CH2:25]([O:24][C:22]([NH:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]=[N+:10]=[N-:11])=[CH:12][CH:13]=1)=[NH:2])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformate2×HCID 222576054-Amidino benzyl azide

Product 1

HCID 140379073benzyl N-[4-(azidomethyl)benzenecarboximidoyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an additional 2 ml benzyl chloroformate was added and stirring was continued for another 30 minutes. Subsequently, water was added and the aqueous phase was adjusted to pH 7 with 2M HCl. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. 4-(benzyloxycarbonylamidino) benzyl azide was finally isolated as colorless crystals from ether/methylene chloride/hexane.

Workup

  1. dry with materialthe resulting solution was dried (K2CO3)
  2. filtrationfiltered
  3. temperaturewas cooled in an ice bath
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-720eb10349c84575816ddda2b033833a
Source dataset
uspto-grants-1999_08
Patent number
US05939392

Linked notes

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