Ammonia → HCID 15383363, compound

HRID 323796Notes

Reaction equation

HRID 323796 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[CH:12]=[C:11]([S:13](=[O:16])(=[O:15])[NH2:14])[CH:10]=[CH:9][C:8]=1[Cl:17])[OH:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>N1C=CC=CC=1>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[C:11]([S:13](=[O:16])(=[O:15])[NH2:14])[CH:10]=[CH:9][C:8]=1[Cl:17])[OH:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 22007155HCID 22007155, compound

Product 1

HCID 15383363HCID 15383363, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.35 g (4.9 mmol) of α-azidomethyl-2-chloro-5-sulphamoylbenzenemethanol, 90 ml of anhydrous pyridine and 9.67 g (29.0 mmol) of triphenylphosphine on a carrier are introduced into a 250-ml round-bottomed flask. The mixture is stirred at room temperature for 9 hours, 100 ml of 28% aqueous ammonia are then added, and the suspension is stirred for 16 hours and filtered. The filtrate is concentrated and the residue is recrystallized in methanol. 0.523 g of α-aminomethyl-2-chloro-5-sulphamoylbenzenemethanol is obtained. 1 equivalent of methanesulphonic acid in 2M solution in methanol is added. After recrystallization in methanol and diethyl ether and drying in a desiccator under vacuum over phosphorus pentoxide, 0.439 g of α-aminomethyl-2-chloro-5-sulphamoylbenzenemethanol methanesulphonate is obtained.

Workup

  1. stirringthe suspension is stirred for 16 hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. customthe residue is recrystallized in methanol

Sources & evidence

ORD record
ord-ede3f16b61844c0f8230b6939b3c04ff
Source dataset
uspto-grants-2001_04
Patent number
US06214882B1

Reaction notes

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