Acetaldehyde → HCID 18967858, compound

HRID 399507Notes

Reaction equation

HRID 399507 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:35])[NH:30][C:29]3=[O:36])[C:9]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[O:10])=[CH:4][CH:3]=1.[CH:37](=O)[CH3:38].C([BH3-])#N.[Na+].Cl>CO.[Ti](Cl)(Cl)(Cl)Cl>[CH2:37]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:35])[NH:30][C:29]3=[O:36])[C:9]([NH:11][S:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:24])([CH3:22])[CH3:23])=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[O:10])=[CH:6][CH:7]=1)[CH3:38]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 18967860HCID 18967860, compound

Product 1

HCID 18967858HCID 18967858, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 6 g of 2-(4-aminophenyl)-2-(1,3-dihydro-1,3-dioxoisoindol-5-yloxy)-N-(4-tert-butylphenylsulfonyl)acetamide and 0.5 g of titanium tetrachloride in 100 ml of methanol is treated with 1 ml of freshly distilled acetaldehyde. 4 g of sodium cyanoborohydride are then added and the mixture is stirred for 30 hours. Half-concentrated hydrochloric acid is added, the mixture is worked up in the customary manner and 2-(4-ethylaminophenyl)-2-(1,3-dihydro-1,3-dioxo-isoindol-5-yloxy)-N-(4-tert-butylphenylsulfonyl)-acetamide is obtained.

Sources & evidence

ORD record
ord-fb43a013b6564d0d8b8962a1e5a56bf2
Source dataset
uspto-grants-1998_10
Patent number
US05821256

Reaction notes

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