Hydrochloric Acid → HCID 21781558, compound

HRID 1196631Notes

Reaction equation

HRID 1196631 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[NH2:16][CH2:17][CH2:18][CH:19]1[CH2:23][C:22]2[C:24]([CH3:38])=[C:25]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]([CH3:29])=[C:27]([CH3:28])[C:21]=2[O:20]1.Cl>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:31]([O:30][C:25]1[C:26]([CH3:29])=[C:27]([CH3:28])[C:21]2[O:20][CH:19]([CH2:18][CH2:17][NH:16][C:6](=[O:7])[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=3)[CH2:23][C:22]=2[C:24]=1[CH3:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 19899203HCID 19899203, compound

Product 1

HCID 21781558HCID 21781558, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 2.86 g of 3,4,5-trimethoxybenzoyl chloride in 35 ml of chloroform is slowly added to a 3.85 g solution of 2-(RS)-(2-aminoethyl)-2,3-dihydro-5-benzyloxy-4,6,7-trimethyl-benzofurane in 35 ml of chloroform and 2.0 ml of triethylamine. After stirring for one hour at room temperature, 1 M hydrochloric acid is added and the organic phase is separated and washed in a sodium bicarbonate solution, dried and evaporated. 4.42 g of--a white solid are obtained that is purified by crystallization from ethanol/ethyl acetate. m.p. 171°-173° C. IR(KBr): 3271 (νN--H), 1684, 1545 cm-1 (νCONH); 1H-NMR (CDCl3): δ7.4-7.2 (5H,m), 7.0 (2H,s), 6.8 (1H,t), 5.1-4.7 (1H,m), 4.7 (2H,s), 3.8 (9H,s), 3.8-3.4 (2H,m), 3.2-2.7 (2H,m), 2.2 (6H,s), 2.1 (3H,s), 2.1-1.8 (2H,m).

Workup

  1. customthe organic phase is separated
  2. washwashed in a sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. custom4.42 g of--a white solid are obtained
  6. customthat is purified by crystallization from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-34392900b248461c9130a23990ea42ac
Source dataset
uspto-grants-1992_05
Patent number
US05114966

Reaction notes

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