Phenyl isocyanate → 1-(6-(3-Phenylaminocarbonylamino-propanoyl)-2-benzothiazolyl)-3-ethylurea

HRID 9140

Reaction equation

HRID 9140 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=2[CH:7]=1)=[O:5].C(N(CC)CC)C.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[C:28]1([NH:34][C:35]([NH:1][CH2:2][CH2:3][C:4]([C:6]2[CH:20]=[CH:19][C:9]3[N:10]=[C:11]([NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15])[S:12][C:8]=3[CH:7]=2)=[O:5])=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 219855561-(6-(3-Aminopropanoyl)-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855861-(6-(3-Phenylaminocarbonylamino-propanoyl)-2-benzothiazolyl)-3-ethylureaYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea (0.033 g, 0.10 mmol) in 1 mL anhydrous DMF was treated with triethylamine (0.028 mL, 0.20 mmol, 2.0 eq) at room temperature. It was stirred for about 5 min, followed by the addition of phenyl isocyanate (0.013 mL, 0.12 mmol, 1.2 eq). It was stirred for about 2.5 hours, quenched with MeOH, filtered, concentrated, and purified by HPLC to give the desired compound 0.009 g (22%). LC/MS 412.2 (M+1); LC retention time 2.80 min.

Workup

  1. stirringIt was stirred for about 2.5 hours
  2. customquenched with MeOH
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-7c11d59354d54b46b7c009458d9fc655
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

Loading…