2-Amino-4-methylbenzothiazole → HCID 21256500, compound

HRID 635863Notes

Reaction equation

HRID 635863 reaction equation
C([O:3][C:4]([C:6]1[N:13]2[C:9]([S:10][C:11]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=32)=[N:8][CH:7]=1)=O)C.NC1SC2C=CC=C(C)C=2N=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]3[C:6]([CH2:4][OH:3])=[CH:7][N:8]=[C:9]3[S:10][C:11]=2[CH:17]=1

Participants

5

Reactant 3

HCID 151322-Amino-4-methylbenzothiazoleHCID 21226445Aluminium lithium hydrideHCID 54166243HCID 54166243, compound

Product 1

HCID 21256500HCID 21256500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-fluoroimidazo[2,1-b]benzothiazole-3-carboxylic acid ethyl ester, (synthesized from 2-amino-methylbenzothiazole according to a modification of the procedures described by Fajeli et al., Heterocycles, 1986, 24, 379) (1.93 g) in dry THF (50 mL) at 0° was treated with LiAlH4 (0.36 g) and reacted at 25° for one hour. The suspension was quenched by serial addition of water and 15% sodium hydroxide. The suspension was filtered and the filtrate was evaporated to yield crude 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) (1.59 g). Crystallization of crude 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) from acetonitrile gave pure 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) (1.3 g), m.p. 240-241°.

Workup

  1. customat 0°
  2. customreacted at 25° for one hour
  3. customThe suspension was quenched by serial addition of water and 15% sodium hydroxide
  4. filtrationThe suspension was filtered
  5. customthe filtrate was evaporated
  6. customto yield crude 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) (1.59 g)
  7. customCrystallization of crude 7-Fluoro-imidazo[2,1-b]benzothiazole-3-methanol (Formula L-2) from acetonitrile

Sources & evidence

ORD record
ord-4f2fdfcea05a48f28629e0ee8ad41c40
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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