Sodium hydride → HCID 21507487, compound

HRID 1287228Notes

Reaction equation

HRID 1287228 reaction equation
[H-].[Na+].[NH:3]1[C:8](=[O:9])[CH2:7][S:6][C:5]2[N:10]=[CH:11][CH:12]=[CH:13][C:4]1=2.[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18]Cl>C1(C)C=CC=CC=1>[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18][N:3]1[C:8](=[O:9])[CH2:7][S:6][C:5]2[N:10]=[CH:11][CH:12]=[CH:13][C:4]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 29110Abbott 29590HCID 669603-Chloro-N,N-dimethyl-1-propanamine

Product 1

HCID 21507487HCID 21507487, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 50% oil dispersion of NaH (7.8 g; 0.16 mole) is added to a stirred suspension of 26 g (0.16 mole) of 1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one in 525 ml of toluene and the mixture gradually warmed, effervescence occurs at about 90°. After heating to reflux for 45 minutes, the mixture is cooled to 30°, treated with 120 ml (0.22 mole) of a 1.8 N toluene solution of 3-dimethylaminopropyl chloride and refluxed for 4 hours. After standing overnight, the mixture is worked up as described in Example 1, part A, to give 23 g of crude base. This is combined with 10 g of base from an earlier experiment and distilled; yield, 27.3 g; bp. 166°-169°/0.2 mm.

Workup

  1. temperaturethe mixture gradually warmed
  2. customoccurs at about 90°
  3. temperatureAfter heating
  4. temperatureto reflux for 45 minutes
  5. temperaturethe mixture is cooled to 30°
  6. temperaturerefluxed for 4 hours

Sources & evidence

ORD record
ord-9fd3e84d3eb8454888cdb02dbdc4d928
Source dataset
uspto-grants-1976_10
Patent number
US03984405

Reaction notes

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