tert-Butyl isocyanate → HCID 54056764, compound

HRID 1379283Notes

Reaction equation

HRID 1379283 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:8][CH2:9][CH2:10][CH:11]([OH:25])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)=[O:13]>C(N(CC)CC)C>[C:1]([NH:5][C:6]([O:25][CH:11]([CH2:10][CH2:9][Cl:8])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanate2×HCID 22909958HCID 22909958, compound

Product 1

HCID 54056764HCID 54056764, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

t-Butylisocyanate (0.093 g) and triethylamine (0.095 g) were added successively to a stirred solution of 4-chloro-2-hydroxy-N(3-trifluoromethylphenyl)butanamide (0.24 g, prepared as described in Example 10, Step 1a above). After a day further aliquots of t-butylisocyanate and triethylamine were added. After a further twenty hours, the mixture was evaporated under reduced pressure and the residue chromatographed under reduced pressure to give the title compound (0.13 g, m.p. 115°-116° C.). NMR (CDCl3): δ 1.4(9H,s); 2.4(2H,m); 3.65(1H,t); 5.0(1H,bs); 5.35(1H,t); 7.35(2H,m); 7.7(1H,d); 7.8(1H,s); 8.6(1H,bs). MS: MH+ 381, 383.

Workup

  1. waitAfter a further twenty hours
  2. customthe mixture was evaporated under reduced pressure
  3. customthe residue chromatographed under reduced pressure

Sources & evidence

ORD record
ord-17ec564291c640538fd9d8b46fd161a4
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

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