Iodine → 2-(N-methyl-3-iodo-2-propynylamino)benzothiazole

HRID 485042Notes

Reaction equation

HRID 485042 reaction equation
[CH3:1][N:2]([C:6]1[S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)[C:3]#[C:4][CH3:5].[OH-].[K+].[I:17]I>CO.O>[CH3:1][N:2]([CH2:3][C:4]#[C:5][I:17])[C:6]1[S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 202713332-(N-methyl-N-propynylamino)benzothiazole

Product 1

HCID 133448502-(N-methyl-3-iodo-2-propynylamino)benzothiazoleYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Compound (d) (2.02 g) was dissolved in a mixture of methanol (35 ml), water (10 ml) and 86% potassium hydroxide (1.4 g) and then iodine (2.66 g) was added in small portions with stirring under ice-cooling. The mixture was stirred at room temperature for 1.5 hours and then water was added thereto. The resultant crystals were filtered off, washed with water and dried to give 2-(N-methyl-3-iodo-2-propynylamino)benzothiazole (No.2) (3.27 g, yield 100%): mp. 100°-101° C. (decomp.) (acetone-hexane), Hydrochloride: mp. 156°-160° C. (decomp.), Nitrate: mp. 108°-109° C. (decomp.), Hydrobromide: mp. 158°-160° C. (decomp.).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1.5 hours
  3. filtrationThe resultant crystals were filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9765da48aa9c450fb0c2506553f77664
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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