Hexamethylphosphoramide → HCID 24843223, compound

HRID 2071752Notes

Reaction equation

HRID 2071752 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[CH2:4][CH2:5][C:6]([OH:8])=O)[CH3:2].CN(P(N(C)C)(N(C)C)=O)C.S(Cl)(Cl)=O.[CH3:26][O:27][C:28]1[CH:34]=[CH:33][C:32]([S:35]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)(=[O:37])=[O:36])=[CH:31][C:29]=1[NH2:30]>C(OCC)C>[CH2:9]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]([NH:30][C:29]1[CH:31]=[C:32]([S:35]([N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)(=[O:36])=[O:37])[CH:33]=[CH:34][C:28]=1[O:27][CH3:26])=[O:8])[CH3:10]

Participants

6

Reactant 4

HCID 12679HexamethylphosphoramideHCID 24386Thionyl ChlorideHCID 2422502-Methoxy-5-(morpholine-4-sulfonyl)-phenylamineHCID 247454N,N-Diethyl-beta-alanine

Product 1

HCID 24843223HCID 24843223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a three-neck flask they are introduced 7.2g 3-diethylaminopropionic acid (hydrochloride) and 180 ml hexamethylphosphorotriamide. The suspension is cooled with an ice-bath and then 2,90 ml thionylchloride are added while maintaining the inner temperature between +5° - +10° C. The reaction mixture progressively gives a yellow solution. After 2 hours stirring 10.9 g of 2-methoxy 5-morpholinylsulphonyl aniline are added portionwise and the whole mixture is kept under stirring for 4 hours at room temperature and then let to stand for a night. The dark solution is thereafter diluted with 1 l ethyl ether and it appears a precipitate. After 1 hour standing the precipitate is collected, suction-filtered and washed with acetone. After thoroughly drying the raw product weighing 11.3g is recovered and further recrystallised from acetone.

Workup

  1. temperatureThe suspension is cooled with an ice-bath
  2. temperaturewhile maintaining the inner temperature between +5° - +10° C
  3. customThe reaction mixture progressively gives a yellow solution
  4. additionare added portionwise
  5. waitto stand for a night
  6. waitAfter 1 hour standing
  7. customthe precipitate is collected
  8. filtrationsuction-filtered
  9. washwashed with acetone
  10. dry with materialAfter thoroughly drying the raw product
  11. customis recovered
  12. customfurther recrystallised from acetone

Sources & evidence

ORD record
ord-289ea098f2484f898ed9c05d511a1a27
Source dataset
uspto-grants-1977_09
Patent number
US04048313

Reaction notes

Loading…