Methanol → HCID 21288865, compound

HRID 867897Notes

Reaction equation

HRID 867897 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:9]1[CH:10]=[C:11]2[N:15]([N:16]=1)[C:14]([C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([N+:25]([O-:27])=[O:26])[C:18]=1[CH3:28])=[N:13][NH:12]2)([CH3:8])([CH3:7])[CH3:6].CO>C1COCC1.N1C=CC=CC=1>[C:1]([N:12]1[C:11]2=[CH:10][C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])=[N:16][N:15]2[C:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([N+:25]([O-:27])=[O:26])[C:18]=2[CH3:28])=[N:13]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 178425653HCID 178425653, compound

Product 1

HCID 21288865HCID 21288865, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (12 g, 154 mmole) in THF (80 ml) was added dropwise to a stirred solution of Coupler 1 (22.5 g, 65.2 mmole) in pyridine (110 ml) keeping the temperature below 15° C. The reaction mixture was stirred for a further 2 hours and then added slowly to ice cold water (2000 ml) and methanol (200 ml). After 30 minutes the solid was collected, washed with water, and dried to give the product 24.1 g (100%) m.p. 169°-171° C.

Workup

  1. customthe temperature below 15° C
  2. customAfter 30 minutes the solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b497ed503ffe4fcbb63c056f66b13ed2
Source dataset
uspto-grants-1988_10
Patent number
US04777121

Reaction notes

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