Hydrochloric Acid → HCID 20326853, compound

HRID 372833Notes

Reaction equation

HRID 372833 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[C:4]=1[OH:17].[ClH:18]>C(O)C>[ClH:18].[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:10])([CH3:11])[CH3:12])[CH:6]=[C:5]([C:13]([F:15])([F:16])[F:14])[C:4]=1[OH:17]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 126521452-(Aminomethyl)-4-tert-butyl-6-(trifluoromethyl)phenol

Product 1

HCID 20326853HCID 20326853, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

The solid, the 2-chloroacetyl derivative of 2-aminomethyl-4-(1,1-dimethylethyl)-6-trifluoromethylphenol is dissolved in a mixture of ethanol (75 ml.) and 12 N hydrochloric acid (25 ml.). The mixture is refluxed for 5 hours, cooled to 20° C. and diluted with 12 N hydrochloric acid (150 ml.). Upon cooling to -20° C., the product separates (14 g.). It is crystallized from ethanol-12 N hydrochloric acid (1:4) to obtain pure 2-aminomethyl-4-tertbutyl-6-trifluoromethylphenol hydrochloride, m.p. 202°-204° C. This material is added to 500 ml. of warm water and treated with excess ammonium hydroxide. The precipitate is collected, washed with water, and air dried to give the free base, m.p. about 148° C.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureUpon cooling to -20° C.
  3. customIt is crystallized from ethanol-12 N hydrochloric acid (1:4)

Sources & evidence

ORD record
ord-df1ce4fbca984e95a2ed6531e6f7f0ff
Source dataset
uspto-grants-1978_05
Patent number
US04092414

Reaction notes

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