Ethyl isocyanate → 1-(6-Benzyl-2-benzothiazolyl)-3-ethylurea

HRID 9126

Reaction equation

HRID 9126 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26]>C1(C)C=CC=CC=1>[CH2:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:28]([NH:27][CH2:25][CH3:26])=[O:29])[S:3][C:4]=2[CH:10]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 219855102-Amino-6-benzylbenzothiazole

Product 1

HCID 219856141-(6-Benzyl-2-benzothiazolyl)-3-ethylureaYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 2-amino-6-benzyl-benzothiazole (0.040 g, 0.17 mmol), triethylamine (0.104 mL, 0.77 mmol, 4.5 eq), and ethyl isocyanate (0.049 mL, 0.64 mmol, 3.8 eq) in 1 mL toluene was heated at about 95° C. for about 16 hours. The precipitate was filtered off, washed with Et2O and MeOH, and dried under vacuum to give the desired compound 0.029 g (56%). LC/MS 312.3 (M+1); LC retention time 2.62 min.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O and MeOH
  3. customdried under vacuum

Sources & evidence

ORD record
ord-507cd915806547c7b328f3dffb50e852
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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