tert-Butanol → tert-butyl N-(5-methylthiophen-2-yl)carbamate

HRID 559047Notes

Reaction equation

HRID 559047 reaction equation
C[C:2]1[S:6][C:5]([C:7](O)=O)=[CH:4][CH:3]=1.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[CH3:34][C:35]([OH:38])([CH3:37])[CH3:36]>>[CH3:7][C:5]1[S:6][C:2]([NH:12][C:15](=[O:24])[O:38][C:35]([CH3:37])([CH3:36])[CH3:34])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 6386tert-Butanol2×HCID 8471TriethylamineHCID 747135-Methylthiophene-2-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 716045tert-butyl N-(5-methylthiophen-2-yl)carbamate

Procedure

A solution of 5-methyl thiophene-2-carboxylic acid (1.42 g, 10.0 mmol), triethylamine (1.50 mL, 10.8 mmol) and diphenyl phosphoryl azide (2.15 mL, 10.0 mmol) in tBuOH (20 mL) was stirred at reflux for 5 h. tBuOH was removed in vacuo. Et2O and water were added. The organic phase was washed with 5% NaHCO3, then with 1N NaOH, and filtered. The filtrate was dried over Na2SO4, concentrated in vacuo to give tert-butyl 5-methylthiophen-2-ylcarbamate as a solid (0.825 g).

Workup

  1. customwas removed in vacuo
  2. additionEt2O and water were added
  3. washThe organic phase was washed with 5% NaHCO3
  4. filtrationwith 1N NaOH, and filtered
  5. dry with materialThe filtrate was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c5b615c9d59416998ee7e5fe168a143
Source dataset
uspto-grants-2011_11
Patent number
US08063058B2

Reaction notes

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