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

HRID 1956786Notes

Reaction equation

HRID 1956786 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.[O-]S([O-])(=O)=O.[Mg+2]>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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformate2×HCID 24083Sulfuric acid magnesium salt (1:1)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 dries (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. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5a8cc25184054f9e9f979b9a2d2552b5
Source dataset
uspto-grants-1998_07
Patent number
US05780631

Reaction notes

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