Ammonia → HCID 21527600, compound

HRID 1658486Notes

Reaction equation

HRID 1658486 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:20])[CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][C:13](=[O:19])[NH:14]2)([CH3:4])([CH3:3])[CH3:2].[C:21](O)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N>CN(C)P(=O)(N(C)C)N(C)C>[C:21]([O:20][CH:7]([CH2:6][NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][C:13](=[O:19])[NH:14]2)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 243Benzoic AcidHCID 7167Benzoic anhydrideHCID 21527625HCID 21527625, compound

Product 1

HCID 21527600HCID 21527600, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1 g of 4-(3-tert-butylamino-2-hydroxypropoxy)oxindole is dissolved in 20 cc of hexamethylphosphoric acid triamide and the solution is allowed to stand at room temperature for 16 hours together with 7.9 g of benzoic acid and 0.9 g of benzoic acid anhydride. The mixture is poured into ice water, is rendered alkaline with a 10% ammonia solution and is extracted with methylene chloride. The title compound is obtained as evaporation residue of the methylene chloride phase; the hydrogen oxalate of the title compound crystallizes from ethanol. M.P. 200°-203°.

Workup

  1. extractionis extracted with methylene chloride

Sources & evidence

ORD record
ord-0e507c5bc504416d914d8803f7ae63d7
Source dataset
uspto-grants-1976_06
Patent number
US03965095

Reaction notes

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