Hydrochloric Acid → HCID 178439657, compound

HRID 653079Notes

Reaction equation

HRID 653079 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]#[N:22])=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:23](=[O:25])[CH3:24].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].Cl>O1CCOCC1.O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]3[NH:28][N:27]=[N:26][N:22]=3)=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:23](=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13368598HCID 13368598, compound

Product 1

HCID 178439657HCID 178439657, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
89 °C

Procedure

1-[2-Hydroxy-3-propyl-4-(4-thiocyanomethylphenylmethoxy)phenyl]ethanone (6.0 g; 0.017 m) was dissolved in dioxan:water (80:20; 100 ml) to which was added sodium azide (4.4 g; 0.068 m) and ammonium chloride (1.8 g; 0.034 m). The resulting solution was heated at 89° C. for 18 hours, cooled and poured onto water. The resulting solution was acidified with concentrated hydrochloric acid, filtered and washed with water to leave a white solid. Recrystallised from methanol to give a cream crystalline solid m.p. 160°-161° C.

Workup

  1. temperaturecooled
  2. additionpoured onto water
  3. filtrationfiltered
  4. washwashed with water
  5. customto leave a white solid
  6. customRecrystallised from methanol

Sources & evidence

ORD record
ord-3a7123640f4f4945a9b4a49020831994
Source dataset
uspto-grants-1987_06
Patent number
US04675334

Reaction notes

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