Triethylamine → HCID 178439176, compound

HRID 1382907Notes

Reaction equation

HRID 1382907 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[C:12](/[CH3:23])=[CH:13]/[C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[CH:10]=2)[O:5][CH2:4][CH2:3]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:40][C:41]1[NH:45][N:44]=[N:43][N:42]=1>C(Cl)(Cl)Cl.CN(C)C=O.CN(C)C=O.C(Cl)(Cl)Cl>[NH:42]1[C:41]([NH:40][C:18](=[O:20])[C:17]2[CH:16]=[CH:15][C:14](/[CH:13]=[C:12](/[C:9]3[CH:10]=[C:11]4[C:6](=[CH:7][CH:8]=3)[O:5][CH2:4][CH2:3][C:2]4([CH3:1])[CH3:24])\[CH3:23])=[CH:22][CH:21]=2)=[N:45][N:44]=[N:43]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 6366138(E)-p-(2-(4,4-Dimethylchroman-6-yl)propenyl)benzoic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178439176HCID 178439176, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 21754633chloroform N,N-dimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 0.5 g (1.55 mmole) of 4-[(E)-2-(4,4-dimethyl-6-chromanyl)-2-methylvinyl]benzoic acid in 20 ml of chloroform-N,N-dimethylformamide (1:1) at -25° C., under nitrogen, was added 0.17 g of triethylamine followed by 0.23 g (1.7 mmole) of isobutyl chloroformate. Stirring was continued for 15 minutes at -25° C. and then a solution of 0.177 g (1.7 mmole) of 5-aminotetrazole in 4 ml of N,N-dimethylformamide was added dropwise during 2 minutes. Stirring was continued for 1 hour as the reaction mixture was allowed to warm to 25° C. The reaction mixture was then diluted with 50 ml of chloroform and washed with 50 ml of 1N hydrochloric acid. The insoluble material was recovered by filtration to give a first crop of the title compound. The layers were then separated and the chloroform layer was washed with 1N hydrochloric acid followed by saturated sodium chloride, dried (MgSO4) and concentrated in vacuo. The residue was triturated under hot chloroform and the insoluble material was collected by filtration to give a second crop of the title compound.

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour as the reaction mixture
  3. washwashed with 50 ml of 1N hydrochloric acid
  4. filtrationThe insoluble material was recovered by filtration

Sources & evidence

ORD record
ord-16b79f462cd2454c9247776bd889dcc7
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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