Dimethylformamide → {[10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea

HRID 427094Notes

Reaction equation

HRID 427094 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].CN(C)C=O.[OH:14][C:15]1[C:20]2[C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:26]=3[C:27]([CH3:30])([CH3:29])[O:28][C:19]=2[CH:18]=[C:17]([CH:31]([CH3:39])[CH:32]([CH3:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=1.C(N(CC)CC)C>O>[OH:14][C:15]1[C:20]2[C:21]3[CH2:22][N:23]([CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4])[CH2:24][CH2:25][C:26]=3[C:27]([CH3:29])([CH3:30])[O:28][C:19]=2[CH:18]=[C:17]([CH:31]([CH3:39])[CH:32]([CH3:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 78516(2-Chloroacetyl)ureaHCID 2135435H-(1)Benzopyrano(4,3-c)pyridine, 1,2,3,4-tetrahydro-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-

Product 1

HCID 20388001{[10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridin-2-yl]acetyl}urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.50 g. (0.011 mole) of chloroacetylurea in 25 ml. of dimethylformamide was added dropwise to a stirred solution of 3.57 g. (0.01 mole) of 10-hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine in 20 ml. of dimethylformamide and 1.11 g. (0.011 mole) of triethylamine. After stirring for 24 hours, 65 ml. of water was added dropwise to the stirred mixture. The solid was filtered and recrystallized from acetonitrile, m.p. 131°-133°.

Workup

  1. filtrationThe solid was filtered
  2. customrecrystallized from acetonitrile, m.p. 131°-133°

Sources & evidence

ORD record
ord-aa945844b4f742dea3b89920748a802e
Source dataset
uspto-grants-1979_10
Patent number
US04172943

Reaction notes

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