2-Furanmethanethiol → [6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

HRID 25758Notes

Reaction equation

O1C=CC(CS[CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])[CH:17]=3)[NH:12][C:11]([CH3:28])([CH3:27])[CH:10]=2)=C1.BrCC1[C:40]2[C:35](=[CH:36][CH:37]=[C:38](C3C=CC=CC=3OC)[CH:39]=2)[NH:34]C(C)(C)C=1.C(=O)([O-])[O-].[K+].[K+].C(S)C1OC=CC=1>>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:27])([CH3:28])[CH:10]=[C:9]2[CH2:8][NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Reactant 4

HCID 73632-Furanmethanethiol

HCID 11430Potassium Carbonate

HCID 117411954-(Furan-3-ylmethylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Product 1

HCID 10406857[6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

Procedure

4-(Furan-3-ylmethylsulfanylmethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 80 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 69 mg of potassium carbonate, and 45 μL of furfuryl mercaptan reacted to give 9 mg of the title compound as a foam.

Sources & evidence

ORD record: ord-021f85b5aeea43379c33c8ff003f81a4
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Reaction notes

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