tert-Butyl isocyanate → HCID 86596234, compound

HRID 491010Notes

Reaction equation

HRID 491010 reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])=[O:5].[C:16]([N:20]=[C:21]=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([NH:20][C:21]([S:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])=[O:5])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 69048570HCID 69048570, compound

Product 1

HCID 86596234HCID 86596234, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well stirred mixture of N-(2-mercaptobenzoyl)-β-alaninamide (0.45 g, 2.0 mmol) in 8 ml DMF was added tert-butyl isocyanate (3.0 mmol). The reaction mixture was stirred for 8-10 h at room temp. After completion of the reaction, all of the DMF was removed in vacuo and the residue was treated with ethyl ether. The white precipitate that formed was washed with water, dried in vacuo/CaCl2 and crystallized from acetonitrile. Yield: 89%. 1H NMR (DMSO-d6): 1.30(s, 9H, 3CH3), 2.38(t, 2H, CH2), 3.40(q, 2H, CH2), 6.86(brs, 1H, NH2), 7.30-7.60(m, 5H, Ar—H, NH2), 8.06(s, 1H, NH), 8.26(t, 1H, NH).

Workup

  1. stirringThe reaction mixture was stirred for 8-10 h at room temp
  2. customAfter completion of the reaction
  3. customall of the DMF was removed in vacuo
  4. additionthe residue was treated with ethyl ether
  5. customThe white precipitate that formed
  6. washwas washed with water
  7. dry with materialdried in vacuo/CaCl2
  8. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-aaedc30e6ca043a592772910c768dc43
Source dataset
uspto-grants-2009_05
Patent number
US07528274B2

Reaction notes

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