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Dicyclohexylcarbodiimide → 4-Octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate

HRID 1458493
Notes
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Reaction equation

HRID 1458493 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:23]1[S:27][C:26]2=[N:28][C:29]([C:31]([OH:33])=[O:32])=[CH:30][N:25]2[CH:24]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH2:34]([O:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([C:23]1[S:27][C:26]2=[N:28][C:29]([C:31]([O:33][C:46]3[CH:47]=[CH:48][C:43]([O:42][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:44][CH:45]=3)=[O:32])=[CH:30][N:25]2[CH:24]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 77412Phenol, 4-(octyloxy)-HCID 701107392-Heptylimidazo[2,1-b]-thiazole-6-carboxylic acid

Product 1

HCID 867534624-Octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

1.2 g of N,N'-dicyclohexylcarbodiimide are added in portions to a solution of 1.3 g of 2-heptylimidazo[2,1-b]-thiazole-6-carboxylic acid, 1 g of 4-octyloxyphenol and 0.1 g of 4-(dimethylamino)pyridine in 25 ml of dichloromethane within 10 minutes while stirring. The mixture is stirred overnight at room temperature and then filtered. The filtrate is diluted with dichloromethane, washed with two portions of 50 ml each of saturated sodium carbonate solution and then with water, dried over magnesium sulphate and filtered, and the filtrate is evaporated. Recrystallization of the residue from ethyl acetate/cyclohexane gives 4-octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate, m.p.(C/SA): 112.6° C., c.p.(SA /I): 151.4° C.

Workup

  1. stirringThe mixture is stirred overnight at room temperature
  2. filtrationfiltered
  3. additionThe filtrate is diluted with dichloromethane
  4. washwashed with two portions of 50 ml each of saturated sodium carbonate solution
  5. dry with materialwith water, dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. customRecrystallization of the residue from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-fbd9e94e23914721be1a5ca68e3af958
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05851425

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes