Formaldehyde → HCID 21416290, compound

HRID 1578829Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH:18]2[NH:22][C:21](=[O:23])[NH:20][C:19]2=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].N1CCOCC1.C=O.O1CCN(CN2[C:44](=O)[CH:43]([CH2:46][CH2:47][C:48]3C=C(C(C)(C)C)C(O)=C(C(C)(C)C)[CH:49]=3)NC2=O)CC1.BrCCCCCC>>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH2:17][CH:18]2[N:22]([CH2:44][CH2:43][CH2:46][CH2:47][CH2:48][CH3:49])[C:21](=[O:23])[NH:20][C:19]2=[O:24])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 5

HCID 712Formaldehyde

HCID 8083Morpholine

HCID 81011-Bromohexane

HCID 21416279HCID 21416279, compound

HCID 21416287HCID 21416287, compound

Product 1

HCID 21416290HCID 21416290, compound

Procedure

5-(3',5' -di-tert-butyl-4'-hydroxyphenylethyl)hydantoin is treated with morpholine and formaldehyde according to the procedure of O. O Orazi and R. A. Corral, Tetrahedron, 15, 93 (1961) to prepare the corresponding 3-N-morpholinomethyl-5-(3',5' -di-tert-butyl-4'-hydroxyphenylethyl)hydantoin. This material is then alkylated in the 1-position with 1-bromohexane as described in Example 25. The morpholinomethyl group is removed by subsequent hydrolysis according to the procedure of O. O. Orazi and R. A. Corral, Experientia, 21, 508 (1965) to give 5-(3',5' -di-tert-butyl-4'-hydroxyphenylethyl)-1-n-hexylhydantoin.

Workup

customThe morpholinomethyl group is removed by subsequent hydrolysis

Sources & evidence

ORD record: ord-fcb626fa2a8f4543934f17f8e275f4aa
Source dataset: uspto-grants-1976_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03939175

Reaction notes

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