Acetic Anhydride → [3-[(4-chlorophenyl)sulfanyl]-1-(2-ethoxy-2-oxoethyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-ylidene]amino acetate

HRID 1516983Notes

Reaction equation

HRID 1516983 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[C:24]3[C:23](=[N:25][OH:26])[CH2:22][CH2:21][CH2:20][C:19]=3[N:18]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]=2[CH3:33])=[CH:11][CH:10]=1>C1(C)C(C)=CC=CC=1.C(O)(=O)C>[C:1]([O:26][N:25]=[C:23]1[CH2:22][CH2:21][CH2:20][C:19]2[N:18]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]([CH3:33])=[C:16]([S:15][C:12]3[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=3)[C:24]1=2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 76689533HCID 76689533, compound

Product 1

HCID 86651383[3-[(4-chlorophenyl)sulfanyl]-1-(2-ethoxy-2-oxoethyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-ylidene]amino acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7237O-XyleneSolvent

Procedure

Acetic anhydride (4.33 mL, 45.8 mmol) was added to a slurry of ethyl [3-(4-chlorophenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate (15 g, 38.2 mmol) in xylene (33.75 mL) and acetic acid (3.75 mL) and the mixture stirred at r.t. for around 20 mins. A sample of the title compound was isolated by filtration and dried at 40° C. m/z 435/437 (MH+); 1H NMR: 7.27-7.23 (2H, m), 7.00-6.96 (2H, m), 4.92 (2H, s), 4.19 (2H, q, J=7.1 Hz), 2.68-2.59 (4H, m), 2.19 (3H, s), 1.90 (3H, s), 1.89-1.81 (2H, m), 1.22 (3H, t, J=7.1 Hz).

Sources & evidence

ORD record
ord-360427c843074a9ea361b7bbcfbb4393
Source dataset
uspto-grants-2012_07
Patent number
US08227622B2

Reaction notes

Loading…