Phenyl Isothiocyanate → Ammonium Hydroxide

HRID 447138Notes

Reaction equation

HRID 447138 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:16])[C@@H:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH2:7][CH3:8].[C:17]1([N:23]=[C:24]=[S:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Br-].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[OH-:15].[NH4+:1].[S:25]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:23]=[C:24]1[NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:16])[C@@H:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:12])[F:13])[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 53442637BenzyltrimethylammoniumtribromideHCID 86654760HCID 86654760, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86654762HCID 86654762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound prepared in STEP B above (263 mgs, ca 1.0 mmol) in methylene chloride (10 mL) was added phenyl isothiocyanate (120 μL, 1.00 mmol). The resulting mixture was stirred at room temperature for 1 h, then treated with benzyltrimethylammonium tribromide (389.4 mgs 1.00 mmol). The resulting mixture was then stirred overnight. The reaction was quenched with aqueous sodium bicarbonate and the mixture extracted into methylene chloride. The organic layer was dried over sodium sulfate, then filtered and concentrated to yield a residue which was purified by normal phase column chromatography, eluting with 90:10:1 chloroform:methanol:concentrated ammonium hydroxide to yield (S)—N-(2-(benzo[d]thiazol-2-ylamino)ethyl)-2-(2,2,2-trifluoroacetamido)butanamide as a yellow solid.

Workup

  1. stirringThe resulting mixture was then stirred overnight
  2. customThe reaction was quenched with aqueous sodium bicarbonate
  3. extractionthe mixture extracted into methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a residue which
  8. customwas purified by normal phase column chromatography
  9. washeluting with 90:10:1 chloroform

Sources & evidence

ORD record
ord-2c36f080f741451c993be40351156db2
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

Loading…