Hydrochloric Acid → HCID 178513047, compound

HRID 1699401Notes

Reaction equation

HRID 1699401 reaction equation
C[O-].[Na+].[C:4]([C:7]1[C:17]2[O:16][CH2:15][CH2:14][C:13]([C:18]([O:20]C)=O)=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)([OH:6])=[O:5].Cl.[NH2:23][C:24]([NH2:26])=[NH:25].Cl>CO.CN(C)C=O.O>[C:4]([C:7]1[C:17]2[O:16][CH2:15][CH2:14][C:13]([C:18]([NH:25][C:24]([NH2:26])=[NH:23])=[O:20])=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18319557HCID 18319557, compound

Product 1

HCID 178513047HCID 178513047, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 28% sodium methoxide in methanol (5.5 ml) was added to a solution of methyl 2,3-dihydro-9-carboxy-1-benzoxepin-4-carboxylate (1.5 g) and guanidine hydrochloride (2.9 g) in N,N-dimethylformamide (15 ml) at ambient temperature. The mixture was stirred at the same temperature for 18 hours. The reaction mixture was poured into water and the mixture was adjusted to pH 6.5 with 6N hydrochloric acid. The isolated precipitate was collected by filtration to give (2,3-dihydro-9-carboxy-1-benzoxepin-4-carbonyl)guanidine (1.11 g).

Workup

  1. filtrationThe isolated precipitate was collected by filtration

Sources & evidence

ORD record
ord-ce056e61a10d4da68b857e4d499a8cec
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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