Triethylamine → HCID 59691744, compound

HRID 898162Notes

Reaction equation

HRID 898162 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.CCN(CC)CC.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>C(Cl)Cl>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 741432-Amino-4-methylthiazole

Product 1

HCID 59691744HCID 59691744, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-4-methylthiazole (11.42 g, 0.10 mol) in CH2Cl2 was cooled to 0° C. in an ice bath and treated with Et3N (12.1 g, 0.12 mol). While stirring, the mixture was treated with phenyl chloroformate (15.6 g, 0.10 mol) drop-wise from an addition funnel. After the addition was complete the mixture was stirred for 10 minutes. The reaction mixture was washed with saturated NaHCO3, water, brine and then dried over MgSO4. The solution was filtered and the solvent removed under vacuum in a rotary evaporator and the resulting solid was chromatographed on silica gel (eluting with 40% ethyl acetate/hexane) to give 12 g of the desired carbamate as a white solid. 1H NMR (300 MHz, CDCl3) δ δ 12.38 (bs, 1 H), 7.47-7.40 (m, 2H), 7.30-7.19 (m, 3H), 6.52 (d, J=1.1 Hz, 1H), 2.41 (d,J=0.8 Hz, 3H). Method 2: Synthesis of phenyl 5-acetyl-4-methylthiazol-2-ylcarbamate.

Workup

  1. additionAfter the addition
  2. stirringwas stirred for 10 minutes
  3. washThe reaction mixture was washed with saturated NaHCO3, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed under vacuum in a rotary evaporator
  7. customthe resulting solid was chromatographed on silica gel (eluting with 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c1aab02045574c9199d01b3e10862b87
Source dataset
uspto-grants-2008_04
Patent number
US07351720B2

Reaction notes

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