tert-Butanol → HCID 4935479, compound

HRID 1797164Notes

Reaction equation

HRID 1797164 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:12][C:13]([OH:16])([CH3:15])[CH3:14]>>[C:13]([O:16][C:10](=[O:11])[NH:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)([CH3:15])([CH3:14])[CH3:12]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 944603,5-Dichlorophenyl isocyanate

Product 1

HCID 4935479HCID 4935479, compoundYield 84%

Procedure

A solution of 3,5-dichloro-phenyl isocyanate (5 g, 26.6 mmol) in t-BuOH (100 mL) was heated at 80° C. for 16 h. The mixture was concentrated by rotary evaporation to give a white solid which was triturated with toluene and evaporated to dryness. Addition of toluene and concentration under vacuum gave (3,5-dichloro-phenyl)carbamic acid-tert-butyl ester as a white solid (6 g, 22.9 mmol, 84%). 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 2H), 7.18 (s, 1H), 6.6 (br s, NH), 1.62 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated by rotary evaporation
  2. customto give a white solid which
  3. customwas triturated with toluene
  4. customevaporated to dryness
  5. additionAddition of toluene and concentration under vacuum

Sources & evidence

ORD record
ord-c9fcbc956ef647518494233736175938
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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