Ammonia → HCID 12666304, compound

HRID 373970Notes

Reaction equation

HRID 373970 reaction equation
S(Cl)(Cl)=O.N.[N:6]([CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)C>[NH2:6][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 223906894-(2-Azidoethyl)benzamide

Product 1

HCID 12666304HCID 12666304, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

For the preparation of the starting material of Example 10a, p-(2-bromoethyl)-acetophenone was reacted with sodium azide in dimethylsulfoxide to give p-(2-azidoethyl)acetophenone. Oxidation with sodium hypobromite gave p-(2-azidoethyl)benzoic acid (m.p. 130°-131°, from acetone-hexane), which was converted with thionyl chloride into the corresponding acid chloride and subsequently with ammonia into p-(2-azidoethyl)benzamide. Treatment with triphenylphosphine and hydrolysis gave p-(2-aminoethyl)benzamide, m.p. 132°-133° (from ethanol).

Sources & evidence

ORD record
ord-04b9b47bc904464a805c009040e039ce
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

Loading…