Carbon Dioxide → 4-(2,4-dicarboxyphenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazole

HRID 399637Notes

Reaction equation

HRID 399637 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]=1[C:14]1[N:15]=[C:16]([N:20]([CH:24]([CH:31]2[CH2:33][CH2:32]2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH3:23])[S:17][C:18]=1[CH3:19].BrC(C)[C:36](C1C=CC(Br)=CC=1Br)=[O:37].C1(C(N(CCC)C(N)=S)C2C=CC=CC=2)CC1.[C:64](=[O:66])=[O:65].C([O:69]CC)C>CCCCC>[C:64]([C:7]1[CH:12]=[C:11]([C:36]([OH:37])=[O:69])[CH:10]=[CH:9][C:8]=1[C:14]1[N:15]=[C:16]([N:20]([CH:24]([CH:31]2[CH2:33][CH2:32]2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH3:23])[S:17][C:18]=1[CH3:19])([OH:66])=[O:65]

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 189677542-Bromo-1-(2,4-dibromophenyl)-1-propanone2×HCID 18967810N-(alpha-cyclopropylbenzyl)-N-propylthiourea2×HCID 189678334-(2,4-dibromophenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 189678034-(2,4-dicarboxyphenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazole

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

5 ml of a 1.7M solution of tert-butyllithium in pentane are added, at -70° C., to 1.1 g of 4-(2,4-dibromophenyl)-5-methyl-2-[N-(α-cyclopropylbenzyl)-N-propylamino]thiazole (prepared from 2-bromo-1-(2,4-dibromophenyl)-1-propanone (Compound 14) and N-(α-cyclopropylbenzyl)-N-propylthiourea (Compound 65), according to the process described in Example 1, Step A), dissolved in 30 ml of anhydrous ethyl ether. The temperature is allowed to rise to -50° C. and the mixture is then subjected to the action of carbon dioxide, allowing the temperature to rise to 20° C.

Workup

  1. customto rise to -50° C.
  2. customto rise to 20° C.

Sources & evidence

ORD record
ord-79a105e8bb0e4a459e9296d641bfcd60
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

Loading…