Hydrochloric Acid → HCID 86666621, compound

HRID 587839Notes

Reaction equation

HRID 587839 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21]([C:23]1[CH:37]=[CH:36][C:26]([CH2:27][NH:28]C(=O)OC(C)(C)C)=[C:25]([CH3:38])[CH:24]=1)=[O:22])[CH3:2].Cl>C(O)C.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[NH2:28][CH2:27][C:26]1[CH:36]=[CH:37][C:23]([C:21]([NH:20][C:4]2[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:14]([F:15])([F:16])[F:17])[C:10]([F:11])([F:12])[F:13])=[CH:8][C:3]=2[CH2:1][CH3:2])=[O:22])=[CH:24][C:25]=1[CH3:38]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 86666622HCID 86666622, compound

Product 1

HCID 86666621HCID 86666621, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

Tert-Butyl (4-{[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-carbamoyl}-2-methylbenzyl)carbamate (1.7 g) was dissolved in ethanol (30 ml). To the solution, conc. hydrochloric acid (3 ml) was added and the mixture was stirred under heating at 60° C. for 4 hours. After adjusting to room temperature, the reaction solution was diluted with ethyl acetate and water and neutralized with sodium hydrocarbonate under vigorous stirring. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain 4-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-methyl benzamide as a crude product (0.81 g). Without further purification, the crude product was used for the next reaction.

Workup

  1. customAfter adjusting to room temperature
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-61e2d049e06541e0a1c8986d73f3f1c2
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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