Diethyl Ether → 2-Amino-1-(3-methyl-benzo[b]thiophen-2-yl)-ethanone hydrochloride

HRID 1244340Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])=[O:4].C1N2CN3CN(C2)C[N:16]1C3.C(OCC)C.[Cl:30]C(Cl)Cl>>[ClH:30].[NH2:16][CH2:2][C:3]([C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])=[O:4]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 4101Hexamethylenetetramine

HCID 6212Chloroform

HCID 27798712-Bromo-1-(3-methyl-1-benzothiophen-2-yl)ethan-1-one

Product 1

HCID 219192252-Amino-1-(3-methyl-benzo[b]thiophen-2-yl)-ethanone hydrochlorideYield 93%

Procedure

1.11 g 2-Bromoacetyl-3-methyl-benzothiophene and 0.56 g hexamethylenetetramine in 20 ml trichloromethane were stirred at room temperature for 16 hours. After addition of 15 ml diethylether the mixture was filtered. The solid residue was stirred at room temperature for 3 hours in a mixture of 15 ml methanol and 1.9 ml concentrated hydrochloric acid. The solvents were distilled off and the residue recrystallized from water to yield 0.90 g (93%) 2-amino-1-(3-methyl-benzo[b]thiophen-2-yl)-ethanone hydrochloride as off-white solid; MS (El): m/e=205 (M+, 40%), 175 (M-CH2NH2, 100%), 147 (M-COCH2NH2, 20%).

Workup

filtrationwas filtered
distillationThe solvents were distilled off
customthe residue recrystallized from water

Sources & evidence

ORD record: ord-b133dc8666bd4fdb88c069a0a2a80a51
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122545B2

Reaction notes

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