Butyl isocyanate → HCID 14727326, compound

HRID 1284929Notes

Reaction equation

HRID 1284929 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([CH2:16][CH3:17])([OH:15])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[OH:14].[CH2:23]([N:27]=[C:28]=[O:29])[CH2:24][CH2:25][CH3:26]>CN(C)C1C=CN=CC=1.ClCCl>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([CH2:16][CH3:17])([OH:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:28](=[O:29])[NH:27][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9][C:8]=1[O:14][C:28](=[O:29])[NH:27][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 14009067HCID 14009067, compound

Product 1

HCID 14727326HCID 14727326, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6.2 g. of 3-trifluoromethyl-2',4'-dihydroxy-α-ethyl-benzhydrol, 4.4 g. of butyl isocyanate and 0.06 g. of 4-dimethylamino-pyridine in 40 ml. of dichloromethane are refluxed for 60 minutes. The reaction mixture is cooled down, and the organic phase is extracted with a 5% aqueous potassium hydroxide solution and washed to neutral with water. The organic phase is dried over anhydrous magnesium sulfate, filtered and solvent is distilled off under reduced pressure. Crystallization of the residue from toluene yields 8.7 g. of the end product, which melts at 110° to 111° C.

Workup

  1. temperatureThe reaction mixture is cooled down
  2. extractionthe organic phase is extracted with a 5% aqueous potassium hydroxide solution
  3. washwashed to neutral with water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationsolvent is distilled off under reduced pressure
  7. customCrystallization of the residue from toluene
  8. customyields 8.7 g

Sources & evidence

ORD record
ord-2612b681e0de46c582075db2191e22a1
Source dataset
uspto-grants-1986_01
Patent number
US04564630

Reaction notes

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