Morpholine → N-(3-(dimethylamino)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

HRID 1258385Notes

Reaction equation

HRID 1258385 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:14][S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:17])=[O:16])[CH:4]=1.N1C[CH2:28][O:27][CH2:26]C1>>[O:27]1[CH2:28][CH2:23][N:2]([C:3]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[N:14][S:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:17])[CH:4]=2)[CH2:1][CH2:26]1.[CH3:1][N:2]([CH3:23])[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:14][S:15]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:17])[CH:4]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 67329790N-(3-(dimethylamino)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

Product 2

HCID 67329790N-(3-(dimethylamino)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamideYield 93.6%HCID 67331243N-(3-morpholino-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

Procedure

N-(3-morpholino-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13c) was prepared according to the procedure for 13b except using 0.2 eq. morpholine, which afforded the title compound 36.3 mg (93.6%) as a wine-red solid, m.p.: 195° C. (dec.).

Sources & evidence

ORD record
ord-911b34e30db24b308ad3088c328bfd26
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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