Formic Acid → 1-(5-(Benzyloxy)-7-formylbenzo[d]thiazol-2-yl)-3-ethylurea

HRID 712269Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:24]#N)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=[O:27]>O.[Al].[Ni]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[O:27])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

1-(5-(Benzyloxy)-7-cyanobenzo[d]thiazol-2-yl)-3-ethylurea (1.00 g, 2.84 mmol) was stirred in formic acid (75 ml) and water (20 ml). Aluminum Nickel alloy (5.5 g, 64.7 mmol) was added and the reaction was stirred at 95° C. for 5 h under N2. LCMS indicated 60% conversion to the desired aldehyde. The reaction was allowed to cool then the volatiles were removed under reduced pressure. The resulting concentrated solution was neutralized to pH9 with a 2M aqueous solution of sodium hydroxide then extracted with EtOAc, the combined extracts concentrated and the resulting residue purified by column chromatography eluting with EtOAc 50 to 100% in petroleum-ether to afford the aldehyde as a yellow solid (200 mg, 99% purity by LC-MS) (20%).

Workup

temperatureto cool
customthe volatiles were removed under reduced pressure
extractionthen extracted with EtOAc
concentrationthe combined extracts concentrated
customthe resulting residue purified by column chromatography
washeluting with EtOAc 50 to 100% in petroleum-ether

Sources & evidence

ORD record: ord-89125e1d6dff48e9a1c92e32b48fe675
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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