Triethylamine → HCID 68556333, compound

HRID 2066444Notes

Reaction equation

HRID 2066444 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.CC[N:14](CC)CC.[CH3:19][C:20]([O:23][C:24]([O:26]C(OC(C)(C)C)=O)=O)([CH3:22])[CH3:21]>C1COCC1.CN(C1C=CN=CC=1)C>[C:24]([C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([NH2:14])=[C:7]([CH3:11])[C:5]=2[N:6]=1)([O:23][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151322-Amino-4-methylbenzothiazoleHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 68556333HCID 68556333, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 2-Amino-4-methyl benzothiazole (25.0 g, 152 mmol) in 456 mL of dry THF was treated with Et3N (42 mL, 300 mmol), (Boc)2O (40.0 g, 183 mmol) and DMAP (3.7 g, 30 mmol) at 20° C. and stirred at 30° C. for 12 h. The resulting solution was concentrated in vacuo, diluted with EtOAc (200 mL) and filtered through a glass filter (Celite) washing with EtOAc (200 mL). The filtrate was washed with NaHCO3 (saturated aqueous solution, 100 mL) and NaCl (saturated aqueous solution, 100 mL), dried over MgSO4 and concentrated in vacuo. The residue was filtered through a silica gel plug (flash column chromatography) eluting with toluene:Et2O=15:1 to 8:1 to afford 2-Boc-amino-4-methyl benzothiazole as a colorless oil (41.4 g, quant.) Rf=0.48 (toluene:Et2O=10:1); 1H NMR (400 MHz, CDCl3) δ 9.75 (1H, br s), 7.61 (1H, d, J=7.8 Hz), 7.19 (3H, m), 2.64 (3H, s), 1.47 (9H, s).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. additiondiluted with EtOAc (200 mL)
  3. filtrationfiltered through a glass
  4. filtrationfilter (Celite)
  5. washwashing with EtOAc (200 mL)
  6. washThe filtrate was washed with NaHCO3 (saturated aqueous solution, 100 mL) and NaCl (saturated aqueous solution, 100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. filtrationThe residue was filtered through a silica gel plug (flash column chromatography)
  10. washeluting with toluene

Sources & evidence

ORD record
ord-7b64842ddc624f1bbb1ccb1d924a9fd1
Source dataset
uspto-grants-2012_10
Patent number
US08293743B2

Reaction notes

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