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Aminoacetonitrile → N-(1,3-benzothiazol-2-yl)-2-cyanoacetamide

HRID 1472142
Notes
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Reaction equation

HRID 1472142 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](N1C=CN=C1)=[O:12].[NH2:18][CH2:19][C:20]#N.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:12])[CH2:20][C:19]#[N:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10901AminoacetonitrileHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 59418727N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide

Product 1

HCID 4530340N-(1,3-benzothiazol-2-yl)-2-cyanoacetamideYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

0.3 g of benzothiazole was dissolved in 50 ml of tetrahydrofuran, and then 0.32 g of carbodiimide was added thereto in a dropwise manner in ice-bath. The obtained reaction mixture was stirred at room temperature for 10 hours. The produced white solid was filtrated, to obtain N-(benzo[d]thiazole-2-yl)-1H-imidazole-1-carboxamide (0.261 g, 54%). N-(benzo[d]thiazole-2-yl)-1H-imidazole-1-carboxamide (30 mg) was dissolved in 5 ml of tetrahydrofuran, and 11.1 mg of 2-aminoacetonitrile and then 29 μl of acetic were added thereto in a dropwise manner. The obtained reaction mixture was stirred at 30° C. for 18 hours, to produce N-(benzo[d]thiazole-2-yl)-2-cyanoacetamide (10 mg) in a light brown solid phase

Workup

  1. customThe obtained reaction mixture

Sources & evidence

ORD record
ord-4738b992765d40819015ee85b43b7766
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012481B2

Reaction notes

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