Epichlorohydrin → HCID 20311967, compound

HRID 2420521Notes

Reaction equation

HRID 2420521 reaction equation
[NH2:1][CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH2:15]([CH:17]1[O:19][CH2:18]1)[Cl:16]>>[CH:13]1[C:14]2[CH:2]([NH:1][CH2:18][CH:17]([OH:19])[CH2:15][Cl:16])[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 7835EpichlorohydrinHCID 10671Fluoren-9-amine

Product 1

HCID 20311967HCID 20311967, compound

Procedure

18.1 g of 9-aminofluorene are reacted with epichlorohydrin, following the procedure described in Example 47, to give 1-(9-fluorenylamino)-2-hydroxy-3-chloropropane, from which, without purification, (9-fluorenylaminomethyl)oxirane is obtained with methanolic sodium hydroxide solution, by the procedure described in Example 48. Reaction of this compound with 17.8 g of 4-trans-propenylguaethol gives 16.1g = 38.7% of theory of 1-(2-ethoxy-5-trans-propenyl-phenoxy)-2-hydroxy-3-(9-fluorenylamino)-propane, which crystallizes out from the reaction solution in the cold in the form of the free base. Colorless crystals which have a melting point of 119°-121° and are identical to the product described in Example 28.

Sources & evidence

ORD record
ord-19e3d0b0f30b48629b83553c75a2baf7
Source dataset
uspto-grants-1978_08
Patent number
US04110472

Reaction notes

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