Hydrochloric Acid → (R)-N-(2-Chloro-3-nitro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120370Notes

Reaction equation

HRID 2120370 reaction equation
Cl.[Cl:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([I:12])[CH:6]=[CH:5][C:4]=1[NH:13][C:14](=[O:26])[C@:15]([O:21][Si](C)(C)C)([CH3:20])[C:16]([F:19])([F:18])[F:17]>CO>[Cl:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([I:12])[CH:6]=[CH:5][C:4]=1[NH:13][C:14](=[O:26])[C@:15]([OH:21])([CH3:20])[C:16]([F:18])([F:19])[F:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69824807(R)-N-(2-chloro-3-nitro-4-iodophenyl)-2-trimethylsilyloxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 69882875(R)-N-(2-Chloro-3-nitro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M Hydrochloric acid (2.5 ml) was added to a solution of (R)-N-(2-chloro-3-nitro-4-iodophenyl)-2-trimethylsilyloxy-2-methyl-3,3,3-trifluoropropanamide (Method 69) (1150 mg) in MeOH (25 ml) and the reaction mixture was stirred for 4 hours at ambient temperature. The volatile material was removed by evaporation and the residue was partitioned between EtOAc (150 ml) and water (75 ml). The organic phase was separated, washed with brine (75 ml) and dried. The volatile material was removed by evaporation to give the title compound (943 mg). NMR: 1.58 (s, 3H), 7.70 (d, 1H), 8.00 (d, 1H); m/z 437.

Workup

  1. customThe volatile material was removed by evaporation
  2. customthe residue was partitioned between EtOAc (150 ml) and water (75 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (75 ml)
  5. customdried
  6. customThe volatile material was removed by evaporation

Sources & evidence

ORD record
ord-8d96ea256d0343199d7ffdf3bf6c278f
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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