Butylamine → HCID 1713561, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH2:13][Cl:14].[CH2:15]([NH2:19])[CH2:16][CH2:17][CH3:18]>>[CH2:15]([NH:19][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH2:13][NH:19][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:16][CH2:17][CH3:18].[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH2:13][Cl:14]Participants
Procedure
14.70 grams (0.0477 mol) 1,2-bis(2-n-butylaminoethoxy)benzene [obtained from the reaction of 1,2-bis(2-chloroethoxy)benzene and n-butylamine] and 11.21 grams (0.0477 mol) 1,2-bis(2-chloroethoxy)benzene were dissolved in 120 ml of N-methylpyrrolidone. The solution was heated under nitrogen at 120-125° C. for 1 hour and then 5 grams anhydrous sodium carbonate was added and the solution was further heated at 120-125° C. for 16 hours. Three portions of sodium carbonate (3 grams each) were then added at one hour intervals for a total heating time of 20 hours. The solvent was removed under vacuum, and the residue dissolved in toluene and the solution washed with water. The toluene solution was evaporated to leave a semi-solid which was triturated with ethanol. The crystalline precipitate which was obtained was filtered and recrystallized from cyclohexane to give the crown ether of formula XV where R is n-butyl in an amount equal to 8.19 grams (36.7% yield). The melting point of this product was 151-152° C. The structure of this crown ether compound was established by the analyses for the elements which were as follows:
Sources & evidence
- ORD record
- ord-60fa7bb2e444411a87f168bc6bfba50b
- Source dataset
- uspto-grants-1978_04
- Patent number
- USRE029616
Reaction notes
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