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

HRID 9128

Reaction equation

HRID 9128 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>C1(C)C=CC=CC=1>[Br:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:22]([NH:21][CH2:19][CH3:20])=[O:23])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 851492-Benzothiazolamine, 6-bromo-

Product 1

HCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylureaYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-amino-6-bromo-benzothiazole (6.12 g, 26.2 mmol), triethylamine (7.30 mL, 52.4 mmol, 2.0 eq), and ethyl isocyanate (4.15 mL, 52.4 mmol, 2.0 eq) in 50 mL toluene was heated at about 90° C. for about 15 hours. The precipitate was filtered off, washed with Et2O, and dried under vacuum to give the desired compound 7.39 g (94%). LC/MS 300.0 (M−1); LC retention time 3.01 min.

Workup

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

Sources & evidence

ORD record
ord-b5f2f4212b8240a4b4901953e91f7565
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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