Ammonia → HCID 21781568, compound

HRID 1196638Notes

Reaction equation

HRID 1196638 reaction equation
C([S:4][CH2:5][CH2:6][CH:7]1[CH2:11][C:10]2[C:12]([CH3:19])=[C:13]([OH:18])[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1)(=O)C.N>CC(C)=O>[SH:4][CH2:5][CH2:6][CH:7]1[CH2:11][C:10]2[C:12]([CH3:19])=[C:13]([OH:18])[C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21781567HCID 21781567, compound

Product 1

HCID 21781568HCID 21781568, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5.1 g of 2-(RS)-(2-acetylthioethyl)-2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofurane in 90 ml of acetone is treated with 20 ml of a 25% NH3 solution under nitrogen and stirred for 16 hours. After acidification, the mixture is extracted with ethyl acetate, and the extracts are dried and evaporated. The obtained 4.3 g of a white solid is obtained that can be crystallized with benzene. m.p. 163°-165° C.; IR (KBr): 3351 (νOH), 1237 cm-1 (νAr--O--CH); 1H-NMR (DMSO-d6): δ5.1-4.4 (1H,m), 3.5 (1H, sb), 3.2-2.6 (4H,m), 2.1 (2H,m), 2.0 (6H,s), 1.95 (3H,s), 1.2 (1H,m).

Workup

  1. extractionAfter acidification, the mixture is extracted with ethyl acetate
  2. customthe extracts are dried
  3. customevaporated

Sources & evidence

ORD record
ord-4da202d887fb4f2f89a6c2ca87a2a358
Source dataset
uspto-grants-1992_05
Patent number
US05114966

Reaction notes

Loading…