Hydrochloric Acid → 4-Hydroxymethyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

HRID 2308438Notes

Reaction equation

HRID 2308438 reaction equation
[CH:1]([C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].O.Cl>C1COCC1>[OH:2][CH2:1][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 222830744-formyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide

Product 1

HCID 98005654-Hydroxymethyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-formyl-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide (194 mg, 0.5 mmol), in THF (40 ml) was added sodium borohydride (19 mg, 0.5 mmol) and the mixture stirred for 2 h at r.t. Water was added (30 ml) followed by 1N HCl (4 ml) and the mixture agitated. The aqueous phase was then extracted twice with EtOAc (30 ml), the combined organic phases were then washed with saturated NaCl solution, dried with Na2SO4 filtered and evaporated. The crude residue was suspended in ether and ultrasonnicated for 10 min., the solid precipitate was filterted off, washed with ether then dried under vacuum (0.05 mmHg, 50° C.) to afford the title compound as a light yellow solid (150 mg, 77% yield), MS: m/e=390.0 (M+).

Workup

  1. stirringthe mixture agitated
  2. extractionThe aqueous phase was then extracted twice with EtOAc (30 ml)
  3. washthe combined organic phases were then washed with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. waitThe crude residue was suspended in ether and ultrasonnicated for 10 min.
  8. washwashed with ether
  9. customthen dried under vacuum (0.05 mmHg, 50° C.)

Sources & evidence

ORD record
ord-45b18197485741a28d7fec8fa4e6d218
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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