Hydrochloric Acid → HCID 57750292, compound

HRID 423106

Reaction equation

HRID 423106 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[NH2:16])=[CH:10]/[C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:16])[CH2:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 57750306(Z)-1-(4-chlorophenyl)-2-(thiazol-2-yl)ethenamine2×

Product 1

HCID 57750292HCID 57750292, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A 2N solution of hydrochloric acid in MeOH at room temperature, was added dropwise to (Z)-1-(4-chlorophenyl)-2-(thiazol-2-yl)ethenamine (Intermediate 94) (1.45 g, 6.13 mmol) and traces of bromocresol green dissolved in MeOH (45 mL) until the solution turned from dark blue to orange. Sodium cyanoborohydride (0.481 g, 7.66 mmol) was added in one portion to the stirred solution and orange color was maintained by adding dropwise the 2N solution of hydrochloric acid in methanol at room temperature. After 1 h stirring, solvent was removed under vacuum. the crude was taken up into water, pH was adjusted around 2 by adding a few drops of the 2N solution of hydrochloric acid in methanol. The aqueous phase was washed with diethyl ether twice then pH was adjusted to 14 by adding a 6N aqueous solution of sodium hydroxide and the basic aqueous phase was extracted with diethyl ether twice. The organic phases were washed with brine dried over magnesium sulphate and concentrated to afford 1-(4-chlorophenyl)-2-(thiazol-2-yl)ethanamine (1.310 g, 90%) as a colorless oil.

Workup

  1. temperaturewas maintained
  2. customsolvent was removed under vacuum
  3. additionby adding a few drops of the 2N solution of hydrochloric acid in methanol
  4. washThe aqueous phase was washed with diethyl ether twice
  5. additionby adding a 6N aqueous solution of sodium hydroxide
  6. extractionthe basic aqueous phase was extracted with diethyl ether twice
  7. washThe organic phases were washed with brine
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-515c8603d63a4e06b4bcd8fad7ec7bd3
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Linked notes

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