Ammonia → HCID 20362849, compound

HRID 1679382Notes

Reaction equation

HRID 1679382 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:21])[CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[C:12]([Cl:20])=[C:13]([CH3:19])[NH:14]2)([CH3:4])([CH3:3])[CH3:2].[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N.C(O)(=O)CC(O)=O>CCOCC.O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[C:22]([O:21][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[C:12]([Cl:20])=[C:13]([CH3:19])[NH:14]2)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 243Benzoic Acid2×HCID 867Malonic AcidHCID 7167Benzoic anhydrideHCID 20362848HCID 20362848, compound

Product 1

HCID 20362849HCID 20362849, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

3.1 g of 1-tert.butylamino-3-(3-chloro-2-methyl-indol-4-yloxy)-2-propanol, 6.1 g of benzoic acid and 12 ml of hexamethyl phosphoric acid triamide are heated on a steam bath until all of the benzoic acid is dissolved. After cooling to room temperature, 2.9 g of benzoic acid anhydride are added and stirring is effected for 15 hours. The resulting clear yellow solution is poured onto ice, 250 ml of ether are added and stirring effected for 1 hour. After making the liquid alkaline with concentrated ammonia, the ether phase is separated, shaken out with tartaric acid, made alkaline while cooling with ice, with concentrated ammonia and extracted with methylene chloride. After evaporating the methylene chloride, the residual title compound is crystallised with 1 mol of malonic acid from tetrahydrofuran and ether. M.p. of hydrogen malonate form: 176°-177°.

Workup

  1. dissolutionis dissolved
  2. additionare added
  3. stirringstirring
  4. waiteffected for 1 hour
  5. customthe ether phase is separated
  6. stirringshaken out with tartaric acid
  7. temperaturewhile cooling with ice, with concentrated ammonia
  8. extractionextracted with methylene chloride
  9. customAfter evaporating the methylene chloride

Sources & evidence

ORD record
ord-34c548c71b34427eb981569c10877d3b
Source dataset
uspto-grants-1978_03
Patent number
US04080463

Reaction notes

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