Hydrochloric Acid → 2-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol

HRID 227237Notes

Reaction equation

HRID 227237 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[S:9][CH:10]=1)=O)C.[BH4-].[Na+].Cl>CCO>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[S:9][CH:10]=[C:6]([CH2:4][OH:3])[N:7]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866229124-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 690554642-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester (292 mg, 1 mmol) was dissolved in 5 mL of absolute EtOH at room temperature in an open flask. Sodium borohydride (1 mmol, 38 mg) was added portionwise over several hours and the reaction was monitored by TLC (EtOAc:hexanes 2:3). After completion of the reaction, 2N HCl was added carefully with stirring. After 15 min, the clear yellow solution was concentrated on the rotavap, and the crude mixture was partitioned between EtOAc (60 mL) and water (60 mL). The organics were isolated and washed with sat NaHCO3 and 60 mL of sat NaCl. The organics were dried over MgSO4, filtered and concentrated to provide an orange solid as the desired material.

Workup

  1. additionwas added carefully
  2. concentrationthe clear yellow solution was concentrated on the rotavap
  3. customthe crude mixture was partitioned between EtOAc (60 mL) and water (60 mL)
  4. customThe organics were isolated
  5. washwashed with sat NaHCO3 and 60 mL of sat NaCl
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0e3cab60644d4dc58b90233874bdd655
Source dataset
uspto-grants-2009_07
Patent number
US07560462B2

Reaction notes

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