Ethyl Acetate → 2-Amino-6-(1,2-dihydronaphthalen-3-yl-methyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

HRID 974287

Reaction equation

HRID 974287 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][C:10]=2[N:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH2:21][CH2:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:19][C:20]3[CH2:21][CH2:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:8][CH2:9][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 127714333-(Chloromethyl)-1,2-dihydronaphthaleneHCID 199857852-Amino-4,5,6,7,8-pentahydrothiazolo[5,4-d]azepine

Product 1

HCID 199859282-Amino-6-(1,2-dihydronaphthalen-3-yl-methyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepineYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine, potassium carbonate and 3-chloromethyl-1,2-dihydronaphthalene (prepared from 1,2-dihydronaphthalene, paraformaldehyde and concentrated hydrochloric acid) in anhydrous dimethylformamide for 2 hours at 50° C. Yield: 29% of theory, Melting point: 158°-160° C. (ethyl acetate).

Sources & evidence

ORD record
ord-61b79b84cbeb4667a54a7c8ecbf62d05
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Linked notes

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