HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Pentylamine → 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)-N-(n-pentyl)thiazole-2-carboxamide

HRID 1392369
Notes
Print preview

Reaction equation

HRID 1392369 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:33]1[CH:38]=[N:37][C:36]2N(O)N=N[C:35]=2[CH:34]=1.F[P-](F)(F)(F)(F)F.ClC1N(C)CC[NH+]1C.C(N)CCCC>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH3:38])=[O:15])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8060PentylamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 218684192-Chloro-1,3-dimethylimidazolidin-1-ium;hexafluorophosphateHCID 692875285-(4-Bromophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid

Product 1

HCID 69290370
5-(4-bromophenyl)-4-(2,4-dichlorophenyl)-N-(n-pentyl)thiazole-2-carboxamide
Yield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Part B: 5-(4-Bromophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid (0.50 gram, 1.17 mmol) and diisopropylethylamine (DIPEA) (1.02 mL, 5.85 mmol) are dissolved in dichloromethane (5 mL) and cooled to 0° C. 7-Aza-1-hydroxybenzotriazole (HOAt) (0.11 gram, 0.81 mmol) and 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate (CIP) (0.50 gram, 1.76 mmol) are added, followed by addition of n-pentylamine (0.15 gram, 1.76 mmol) and the resulting mixture is stirred at room temperature overnight. Flash chromatographic purification (dichloromethane) gives 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)-N-(n-pentyl)thiazole-2-carboxamide as an amorphous solid (0.28 gram, 48% yield).

Workup

  1. customFlash chromatographic purification (dichloromethane)

Sources & evidence

ORD record
ord-332f66f463884bd3b5199b216b54a522
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342032B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes