4-Aminophenol → HCID 71277815, compound

HRID 62115Notes

Reaction equation

HRID 62115 reaction equation
[C:1]([C:3]1[S:4][C:5]2[C:11]([C:12]#[N:13])=[C:10](/[N:14]=[CH:15]/[N:16](C)C)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].N[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[K+].[Br-]>CCOC(C)=O>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([NH:13][C:12]2[C:11]3[C:10](=[CH:9][CH:8]=[C:6]4[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]4=3)[N:14]=[CH:15][N:16]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 71277815HCID 71277815, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared from VII and 4-aminophenol. Flash chromatography eluent (EtOAc). Yield: 80%; orange solid; mp 236° C.; IR (KBr) νmax/cm−1 3072, 2225, 1641, 1615, 1577, 1503, 1464, 1378, 1350, 1307, 1230, 1212, 1159, 1097, 972, 832; 1H NMR (300 MHz, DMSO-d6) δ 8.48 (d, 1H, J=8.7 Hz), 8.08 (m, 1H), 7.76 (d, 1H, J=8.7 Hz), 7.15 (m, 2H), 6.79 (m, 2H); HRMS calcd for C16H10N5OS (M+H+): 320.0606, found 320.0619.

Sources & evidence

ORD record
ord-381bd9c0e6b64cc483ef874fa4a4e7bd
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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