Butyl isocyanate → 1-(3-Trifluoromethylphenyl)-1-(4-butylaminocarbonyloxyphenyl)-1-propanol

HRID 1284927

Reaction equation

HRID 1284927 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([CH2:15][CH3:16])([OH:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25].C(N(CC)CC)C.[OH-].[K+]>C1C=CC=CC=1>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([CH2:15][CH3:16])([OH:14])[C:7]1[CH:8]=[CH:9][C:10]([O:13][C:27](=[O:28])[NH:26][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 1818763-Trifluoromethyl-4'-hydroxy-alpha-ethylbenzhydrol

Product 1

HCID 147273241-(3-Trifluoromethylphenyl)-1-(4-butylaminocarbonyloxyphenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

8.9 g. of 3-trifluoromethyl-4'-hydroxy-α-ethyl-benzhydrol, 3.3 g. of n-butyl-isocyanate and 0.06 ml. of triethyl amine in 45 ml. of dry benzene are heated up to 50° C. under stirring, and the reaction mixture is kept at the same temperature for one additional hour. The progress of the reaction is monitored by thin layer chromatography. When the reaction is complete, the mixture is cooled to room temperature, the benzene solution is shaken with a 5% aqueous potassium hydroxide solution and washed to neutral with water. The organic phase is dried over anhydrous magnesium sulfate, filtered, and the solvent is distilled off under reduced pressure. The solid residue is crystallized from a mixture of ethyl acetate and n-hexane. 11.4 g. of the named compound are obtained, melting at 99° to 100° C.

Workup

  1. washwashed to neutral with water
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe solid residue is crystallized from a mixture of ethyl acetate and n-hexane
  6. customof the named compound are obtained

Sources & evidence

ORD record
ord-f076cec6be3d4570b8a05b9fb53c40d8
Source dataset
uspto-grants-1986_01
Patent number
US04564630

Linked notes

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