Triethylamine → Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

HRID 1076834Notes

Reaction equation

HRID 1076834 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[SH:18].[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]=[C:34]=S)=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[S:18][C:34]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:28][CH:29]=3)=[N:9][C:10]=2[CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidineHCID 121992962-Amino-4-methoxybenzene-1-thiol hydrochloride

Product 1

HCID 38054Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.7 ml.) is added to a suspension of 2-amino-4-methoxybenzenethiol hydrochloride (0.96 g.) in toluene (20 ml.) under nitrogen. 4-(2-Pyrrolidin-1-ylethoxy)phenyl isothiocyanate (1.24 g.) is added and the mixture stirred and heated under reflux for 16 hours. Ethyl acetate and 10% sodium hydroxide are added and the organic layer separated, washed with water and dried. The organic layer is passed through a column of silica gel (2 × 20 cm.) and the filtrate rejected. The column is eluted with methanol, which, on concentration gives 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole, m.p. 167° - 168°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customthe organic layer separated
  4. washwashed with water
  5. customdried
  6. washThe column is eluted with methanol, which, on concentration

Sources & evidence

ORD record
ord-8212335d39954d859208caa13f472fa5
Source dataset
uspto-grants-1976_05
Patent number
US03957999

Reaction notes

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