Ammonia → HCID 3026149, compound

HRID 894979Notes

Reaction equation

HRID 894979 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[ClH:11].C(OCC)C.[NH3:17]>C(O)C>[ClH:11].[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]([NH2:17])=[NH:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 265484-Hydroxybenzyl cyanide

Product 1

HCID 3026149HCID 3026149, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Hydroxybenzyl cyanide (5.0 g) was dissolved in absolute ethanol (50 ml) and the solution saturated with dry HCl gas over 4 hours at ambient temperature. After standing at 4° C. for 72 hours, dry diethyl ether (200 ml) and light petroleum (100 ml) were added and white crystals were deposited over 2 hours. The solid was isolated by filtration and reacted immediately with saturated ethanolic ammonia (300 ml) for 3 hours at ambient temperature. The reaction mixture was evaporated to dryness on a steam bath and the residue recrystallised from ethanol. Yield 4.36 g M.P. 248° C. (dec.) N.M.R. δ(Dimethylsulphoxide d6) 9.0-9.8 envelope 5H exchangeable with D2O, amidine H, hydroxyl H. 6.85+7.37 AA'BB' quartet 4H (J: 9 Hz) phenyl H; 3.70 singlet 2H benzyl H.

Workup

  1. waitwhite crystals were deposited over 2 hours
  2. customThe solid was isolated by filtration
  3. customThe reaction mixture was evaporated to dryness on a steam bath
  4. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-2fd135f692e740e39ee057bda9f535c7
Source dataset
uspto-grants-1981_08
Patent number
US04285932

Reaction notes

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