Water → HCID 178497007, compound

HRID 1898334Notes

Reaction equation

HRID 1898334 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[NH2:17].O.[N:19]#[C:20]Br>C(O)C>[NH2:19][C:20]1[NH:1][C:2]2[C:7]3[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=3[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=2[N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 67503724Methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate

Product 1

HCID 178497007HCID 178497007, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate (Intermediate-1, 2.00 g, 8.47 mmol) in ethanol:water (50:4 mL) was added cyanogen bromide (1.07 g, 10.16 mmol). The reaction mass was refluxed for 4-5 h. The reaction mass was quenched in water, neutralised with sodium bicarbonate and extracted with solution of (10%) DCM: methanol. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 1.0 g of the desired product. 1HNMR (DMSO-d6): δ 1.42 (s, 6H), 3.03 (s, 2H), 3.71 (s, 3H), 6.67 (bs, 2H), 7.33 (s, 1H), 10-11 (bs, 1H). MS [M+H]+: 237.03.

Workup

  1. temperatureThe reaction mass was refluxed for 4-5 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with solution of (10%) DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ded34e6e3ec645db9daa96b5f2afe03b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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