Hydrochloric Acid → Naphtho(1,2-d)thiazol-2-amine, 4,5-dihydro-N-(2-(4-morpholinyl)ethyl)-, dihydrochloride

HRID 2253595Notes

Reaction equation

HRID 2253595 reaction equation
[C:1]([NH:9][C:10]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[S:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[ClH:23].Br[CH:25]1[CH2:34]CC2C(=CC=CC=2)[C:26]1=O>C(O)C>[ClH:23].[ClH:23].[O:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][NH:12][C:10]2[S:11][C:26]3[CH2:25][CH2:34][C:7]4[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:1]=3[N:9]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1011201(2H)-Naphthalenone, 2-bromo-3,4-dihydro-HCID 805795HCID 805795, compound

Product 1

HCID 3088648Naphtho(1,2-d)thiazol-2-amine, 4,5-dihydro-N-(2-(4-morpholinyl)ethyl)-, dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.66 g of N-benzoyl-N'-(morpholinoethyl)thiourea are refluxed in 17.5 ml of a 2.5N solution of sodium hydroxide under a nitrogen atmosphere for 15 minutes. After cooling, concentrated hydrochloric acid is added until the pH is 7. A solution of 3 g of 2-bromo-1,2,3,4-tetrahydronaphthalen-1-one in 20 ml of ethanol is added and the mixture is refluxed for 1 hour. After evaporation of the solvent, the residue is neutralized by the addition of sodium bicarbonate and extraction is carried out twice with methylene chloride. The organic phase is dried over magnesium sulfate and chromatographed on a silica column by elution with a methylene chloride/methanol mixture (95/5 vol/vol).

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture is refluxed for 1 hour
  3. customAfter evaporation of the solvent
  4. additionthe residue is neutralized by the addition of sodium bicarbonate and extraction
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customchromatographed on a silica column by elution with a methylene chloride/methanol mixture (95/5 vol/vol)

Sources & evidence

ORD record
ord-384cd743ff054b4e9b6a3d167e391c45
Source dataset
uspto-grants-1993_08
Patent number
US05232921

Reaction notes

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