4-Methoxy-2-aminobenzothiazole → 1-Benzyl-3-(4-methoxybenzo[d]thiazol-2-yl)urea

HRID 2250715Notes

Reaction equation

HRID 2250715 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1.[CH2:13]([N:20]=[C:21]=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([NH:20][C:21]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 216224-Methoxy-2-aminobenzothiazoleHCID 76639Benzyl isocyanate

Product 1

HCID 222834261-Benzyl-3-(4-methoxybenzo[d]thiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-amino-4-methoxy-benzothiazole (180 mg, 1 mol) in THF (5 ml) was added benzylisocyanate (166 mg, 1.25 mmol) and the mixture heated to 60° C. for 3 h. After evaporation of the solvent, ether (5 ml) was added and the suspension ultra-sonnicated for 10 min with addition of nHexane (5 ml). This suspension was filtered and washed further with ether/nHexane (1:1) to afford the title compound, after drying under vacuum, as a white solid (220 mg, 70% yield), MS: m/e=313 (M+).

Workup

  1. customAfter evaporation of the solvent, ether (5 ml)
  2. additionwas added
  3. additionthe suspension ultra-sonnicated for 10 min with addition of nHexane (5 ml)
  4. filtrationThis suspension was filtered
  5. washwashed further with ether/nHexane (1:1)

Sources & evidence

ORD record
ord-b7c8164b8ce34d86ac8a6c4d2939fade
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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