Methoxyacetic Acid → HCID 21427270, compound

HRID 1606667Notes

Reaction equation

HRID 1606667 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][CH2:7][C:8]([OH:10])=O.[CH3:11][NH:12][C:13](=[O:31])[CH2:14][NH:15][C:16](=[O:30])[C:17]1[C:22]([I:23])=[C:21]([NH2:24])[C:20]([I:25])=[C:19]([C:26]([OH:28])=[O:27])[C:18]=1[I:29].CNC(=O)[C@H](CC1C=CC=CC=1)NC(=O)C1C(I)=C(N)C(I)=C(C(O)=O)C=1I>CC(N(C)C)=O>[CH3:11][NH:12][C:13](=[O:31])[CH2:14][NH:15][C:16](=[O:30])[C:17]1[C:22]([I:23])=[C:21]([NH:24][C:8](=[O:10])[CH2:7][O:6][CH3:5])[C:20]([I:25])=[C:19]([C:26]([OH:28])=[O:27])[C:18]=1[I:29]

Participants

6

Reactant 4

HCID 12251Methoxyacetic AcidHCID 24386Thionyl ChlorideHCID 21427288HCID 21427288, compoundHCID 54110808HCID 54110808, compound

Product 1

HCID 21427270HCID 21427270, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
0 °C

Procedure

At maximally 10° C., 29.0 ml. of thionyl chloride is added dropwise under agitation to 28.2 ml. of methoxyacetic acid in 100 ml. of dimethylacetamide within 40 minutes. After, at 0° C., the reaction mixture has been agitated for another 2 hours, 63.0 g. (0.1 mole) of N-(3-carboxy-5-amino-2,4,6-triiodobenzoyl)-glycine methylamide (IV a), m.p. 252°-253° C. (decomposition), in 100 ml. of dimethylacetamide is added dropwise under agitation to the reaction mixture at maximally 8° C. during the course of one hour. Then, the solution is agitated overnight. After the addition of 5 ml. of water, the mixture is concentrated under vacuum, the residue is stirred with 700 ml. of water, the precipitate is vacuum-filtered, carefully washed with water, and, while still moist, reprecipitated from dilute ammonia with concentrated hydrochloric acid. After allowing the mixture to stand for some time, the acid is vacuum-filtered, washed well with water, stirred with fresh water, and, after another filtering step, dried under vacuum at 70° C.

Workup

  1. customAt maximally 10° C.
  2. stirringThen, the solution is agitated overnight
  3. additionAfter the addition of 5 ml
  4. concentrationof water, the mixture is concentrated under vacuum
  5. stirringthe residue is stirred with 700 ml
  6. filtrationof water, the precipitate is vacuum-filtered
  7. washcarefully washed with water
  8. customwhile still moist, reprecipitated from dilute ammonia with concentrated hydrochloric acid
  9. filtrationthe acid is vacuum-filtered
  10. washwashed well with water
  11. stirringstirred with fresh water
  12. customafter another filtering step, dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-d301aa8be16c48e5892f97bb74ad29e8
Source dataset
uspto-grants-1976_04
Patent number
US03953501

Reaction notes

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