Hydrochloric Acid → HCID 14500505, compound

HRID 1762867Notes

Reaction equation

HRID 1762867 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].O.Cl>CS(C)=O>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][N:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8929Sodium CyanideHCID 14500504HCID 14500504, compound

Product 1

HCID 14500505HCID 14500505, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
64 °C

Procedure

Sodium cyanide (17.2 g, 0.35 mol) was stirred mechanically in 325 mL DMSO under nitrogen and heated to 64° C. The 29.7 g of N-(4-bromobutyl)-N-(4-hydroxyphenyl)trifluoroacetamide in 125 mL of DMSO was dripped in over 13/4 hours. The reaction was stirred for two hours at 65°-72° C., cooled to -15° C., and poured into 3 L of ice and water. The cold mixture was immediately acidified with about 350 mL of 1N HCl and extracted three times with a total of 1.2 L of ethyl acetate. The ethyl acetate extracts were washed once with saturated sodium chloride solution and dried over magnesium sulfate. The solution was evaporated on a rotary evaporator to yield 11.5 g of N-(4-cyanobutyl)-N-(4-hydroxyphenyl)trifluoroacetamide.

Workup

  1. custom4 hours
  2. temperaturecooled to -15° C.
  3. extractionextracted three times with a total of 1.2 L of ethyl acetate
  4. washThe ethyl acetate extracts were washed once with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solution was evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-3af22316daa849f8a4be782772dd8e52
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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