N-(5-Chloro-2-methoxyphenyl)thiourea → N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamide

HRID 1942995Notes

Reaction equation

HRID 1942995 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)=O.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]([NH2:27])=[S:26])[CH:23]=1>CCO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]2[S:26][CH:2]=[C:3]([C:5]3[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=3)[N:27]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 2732660N-(5-Chloro-2-methoxyphenyl)thioureaHCID 25130826N-(5-(2-Bromoacetyl)thiazol-2-yl)pivalamide

Product 1

HCID 25130491N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamideYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 21z (0.73 g, 2.3 mmol) and N-(5-chloro-2-methoxyphenyl)thiourea (0.73 g, 2.53 mmol) in EtOH (25 mL) was refuxed for 30 min. Upon cooling, the product was collected by filtration and washed with cold ethanol to yield 22z as a pale yellow solid (0.40 g, 84%). Mp decomposition at 216° C. 1H NMR (600 MHz, DMSO-d6): δ 11.86 (br s, 1H) 9.93 (br s, 1H), 8.64 (d, J=2.4 Hz, 1H), 7.83 (s, 1H), 7.18 (s, 1H), 7.02 (d, J=8.4 Hz, 1H), 6.98 (dd, J=8.4 Hz, 2.4 Hz, 1H), 3.86 (s, 3H), 1.25 (s, 9H). 13C NMR (150 MHz, DMSO-d6): δ 176.7, 162.1, 158.9, 146.6, 140.2, 136.4, 130.5, 124.7, 124.2, 121.3, 117.3, 112.1, 91.0, 56.1, 38.8, 26.6. HRMS m/z (ESI) calcd. for C18H19ClN4O2S2 (M+H)+ 423.0711. Found 423.0713.

Workup

  1. temperatureUpon cooling
  2. filtrationthe product was collected by filtration
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-13875481471948a38197ae3ab5b2e260
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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