1-Dodecanethiol → 2-amino-N-benzyl-6-hydroxybenzamide

HRID 714551Notes

Reaction equation

[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(S)CCCCCCCCCCC.C[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-amino-N-benzyl-6-methoxybenzamide (0.228 g, 0.89 mmol, 1.0 equiv) in 3 mL of anhydrous DMF was added 1-dodecanethiol (0.360 g, 1.78 mmol, 2.0 equiv), followed by adding NaOMe (0.385 g of 25% solution in MeOH, 1.78, 2.0 equiv). The mixture was heated in a microwave at 150° C. for 10 min. The mixture passed through a silica gel plug, which was washed with an ethyl acetate-methanol mixture (1:1). The crude product was purified by PL-SO3H MP SPE (Varian) to give 2-Amino-N-benzyl-6-hydroxybenzamide (0.176 g, 82%) as thick oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.55-4.20 (vb.s., 2H), 4.60 (s, 1H), 4.61 (s, 1H), 6.25 (d, J=7.8 Hz, 1H), 6.50 (d, J=8.2 Hz, 1H), 7.09 (t, J=8.0 Hz, 1H), 7.16-7.52 (m, 5H), 8.58 (br. s., 1H), 12.05 (br. s., 1H); HPLC: tR=3.97 min, UV254=98%; HRMS (ESI): m/z calcd for C14H14N2O2 [M+1]+ 243.11. found 243.1134.

Workup

washwas washed with an ethyl acetate-methanol mixture (1:1)
customThe crude product was purified by PL-SO3H MP SPE (Varian)

Sources & evidence

ORD record: ord-2844e191ab2742338dc39a117a299a6d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187457B2

Reaction notes

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