Ethyl Acetate → 1-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea

HRID 2383866Notes

Reaction equation

HRID 2383866 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[S:13]1[C:17]2[CH:18]=[C:19]([NH2:22])[CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1.[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH2:27].C(OC(=O)C)C>C1COCC1.CCCCCC>[S:13]1[C:17]2[CH:18]=[C:19]([NH:22][C:2]([NH:27][CH2:26][CH:25]([O:28][CH3:29])[O:24][CH3:23])=[O:4])[CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 682886-AminobenzothiazoleHCID 89728Aminoacetaldehyde dimethyl acetalHCID 94429Triphosgene

Product 1

HCID 687854451-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-ureaYield 228.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

TEA (185 mL, 1.3315 mmol) and triphosgene (138 mg, 0.4660 mmol) were added to a solution of benzothiazol-6-ylamine (200 mg, 1.3315 mmol) in THF (20 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours. This was followed by the addition of 2,2-dimethoxy-ethylamine (173 mL, 1.5978 mmol) in THF and TEA (185 mL, 1.3315 mmol) and the stirring was continued for a further 18 hours at room temperature. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was concentrated and the concentrate was partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (100% ethylacetate) afforded 300 mg of 1-Benzothiazol-6-yl-3-(2,2-dimethoxy-ethyl)-urea (80.21% yield).

Workup

  1. waitthe stirring was continued for a further 18 hours at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate was partitioned between ethylacetate and water
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (100% ethylacetate)

Sources & evidence

ORD record
ord-26481b10f50c4eb3960317e1d630d640
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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