Ammonium Hydroxide → HCID 89907188, compound

HRID 1506850Notes

Reaction equation

HRID 1506850 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11](O)=[O:12])[O:8][C:7]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[CH:26]=1.C(N1C=CN=C1)([N:29]1C=CN=C1)=O.[NH4+].[OH-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([NH2:29])=[O:12])[O:8][C:7]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 13076901HCID 13076901, compound

Product 1

HCID 89907188HCID 89907188, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.8 g 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carboxylic acid and 2.44 g 1,1′-carbonyl diimidazole in 122 ml THF was stirred for 2 h at room temperature. Then 122 ml 25% aqueous NH4OH was added and the reaction mixture stirred for 16 h at room temperature. The precipitate was filtered, washed with cold water and dried over P2O5. Recrystallization from EtOAc yielded the desired product. Yield: 3.55 g.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with cold water
  3. dry with materialdried over P2O5
  4. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-670e3fc7f6964c929aaf772e2f04bd1a
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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