Ammonium Chloride → HCID 66844939, compound

HRID 2064478Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[O:4].[Cl-].[NH4+]>C(O)C.O.C(Cl)Cl.[Fe]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-methyl-5-(3-nitro-phenyl)-thiazole-4-carboxylic acid methyl ester (44.1 mmol) and ammonium chloride (220 mmol) in a mixture of ethanol (100 mL) and water (50 mL) is treated with iron powder (53.0 mmol) and heated to 80° C. After 4 h an additional portion of iron powder (53.0 mmol) is added, the mixture is stirred at 80° C. for 3 h, further iron powder (26.5 mmol) is added and the mixture is again stirred at 80° C. for 3.5 h. The mixture is allowed to reach RT, diluted with DCM and filtered through Celite. The filtrate is concentrated in vacuo and diluted with DCM and sat aqueous NaHCO3 solution. The layers are separated and the organic layer is washed with water, dried over MgSO4 and concentrated in vacuo to give the desired aniline derivative. LC-MS: tR=0.67 min; [M+H]+=249.4.

Workup

stirringthe mixture is again stirred at 80° C. for 3.5 h
customto reach RT
filtrationfiltered through Celite
concentrationThe filtrate is concentrated in vacuo
additiondiluted with DCM
customThe layers are separated
washthe organic layer is washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-89f3139eb38e42538c8594c90ffd2a29
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288429B2

Reaction notes

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