Hydrochloric Acid → HCID 102201652, compound

HRID 1763488Notes

Reaction equation

HRID 1763488 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)[CH:6]=[CH:5][C:4]=1[OH:34].NC1C=C(C2SC3=NCCN3C2)C=CC=1.Cl.C(Cl)Cl.[OH-].[Na+]>CO.O>[CH3:33][O:32][C:27]1[CH:26]=[C:25]([CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9][C:7]2[CH:6]=[CH:5][C:4]([OH:34])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:30]=[CH:29][C:28]=1[OH:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 131711239HCID 131711239, compound

Product 1

HCID 102201652HCID 102201652, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The anhydride prepared in Part B (1.76 g) was added to a solution of dl-6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b] thiazole (880 mg) in cold (0°-10°) aqueous methanol (16 ml methanol/4 ml H2O); the pH of the methanol solution having been adjusted to 5 with dilute hydrochloric acid prior to the addition of the anhydride. The resulting mixture was stirred at room temperature for 24 hours. Methylene chloride (50 ml) and water (5 ml) were then added and the pH was adjusted to 10 with 2N sodium hydroxide. The organic layer was separate, washed with water at pH 6 containing dilute hydrochloric acid to extract unreacted amine into the aqueous phase, separated, and repeatedly washed with dilute aqueous hydrochloric acid at pH 1 to remove further impurities. The aqueous phases from the repeated washings with the pH 1 hydrochloric acid were combined, basified with 2N sodium hydroxide to pH 10, and extracted with methylene chloride. After separation, the organic phase was dried, and the solvent removed by evaporation to yield a white solid, dl-6-(m-(6-bromonicotinoylamino)phenyl9-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole, which was recrystallized from acetone. The yield of the product was 204 mg, melting at 149°-153°, molecular weight from mass spectral data 403.

Workup

  1. customThe organic layer was separate
  2. washwashed with water at pH 6
  3. additioncontaining dilute hydrochloric acid
  4. extractionto extract unreacted amine into the aqueous phase
  5. customseparated
  6. washrepeatedly washed with dilute aqueous hydrochloric acid at pH 1
  7. customto remove further impurities
  8. washThe aqueous phases from the repeated washings with the pH 1 hydrochloric acid
  9. extractionextracted with methylene chloride
  10. customAfter separation
  11. customthe organic phase was dried
  12. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-21e321066bf14186a0d30259ba0081e7
Source dataset
uspto-grants-1978_09
Patent number
US04112102

Reaction notes

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